Mid-Term Rentals

Mid-term rentals compress
long-stay yield against
Caribbean counter-cyclical supply.

The MTR research note recommends piloting mid-term rental (28-to-90-night average stays) inside the existing Caribbean currency block already published in the deck (USD-denominated yield through the 8–12% modelled band) — same operator, same Reg D / Reg S foreign-LP pathway, same founder-sourced acquisition stack — but reframed for a stay-length market segment that absorbs shoulder-season inventory without dropping nightly rate. The thesis below lays out the executive summary, the Caribbean pilot recommendation, and the LP gateway that lets a capital partner opt into the pilot through the existing fractional + single-LP surfaces.

Download the deck (PDF)Talk to a founder about mid-term rentalsRead the underwriting methodology →
Executive summary

The MTR thesis in two blocks.

The mid-term rental pilot does not introduce a new fund vehicle — it is a stay-length positioning inside the existing Caribbean currency block. The two blocks below lay out the segment bet and the counter-cyclical Caribbean supply that absorbs it.

01 · 28-to-90-night stays
Stay-length

MTR compresses long-stay yield against Caribbean shoulder-season supply

Mid-term rental is the 28-to-90-night average-stay segment that sits between long-stay annual leases and the nightly short-term-rental market the deck is built around. The segment compresses per-night revenue against a length-of-stay that absorbs shoulder-season inventory without sliding nightly rate. Acquisitions are founder-network sourced. Local property management, housekeeping, and short-term-rental compliance are run by a Jamaica-based partner team under a single operator playbook — so the acquisition stack is unchanged, and the MTR operator playbook inherits the same founder-network sourcing the Jamaica leg runs on. Illustrative annual net yield band after management fees, platform fees, and a vacancy reserve. Yields projected, not guaranteed. Note: yield figures quoted elsewhere on this site are illustrative short-term-rental targets and not a guarantee of MTR-band outcomes.

Source: caribbean-presets.CARIBBEAN_PILLARS[03] (founder-sourced acquisitions, single operator playbook) · investor-deck.INVESTOR_DECK.terms.targetNetYieldCopy (illustrative yield disclaimer) · roi-presets.MARKETS[caribbean].yieldMin / yieldMax (8–12%)

02 · Caribbean counter-cyclical band
Counter-cyclical

Caribbean supply already absorbs the MTR segment — counter-cyclically

TropicBay target band: 8–12% net (USD-denominated). Airbnb-active since 2016; ~75% occupancy on managed short-term-rental stock in the Montego Bay + Negril corridor. The counter-cyclical Caribbean band sits inside the 2026 carve-out the deck cites for the regional pilot (US leg modelled at 6–8% off-season stabilization; Caribbean at 8–12%) — and the same shoulder-season demand driving the Jamaica nightly-rate floor is the demand an MTR program writes against. Beachfront or near-beachfront resort zone, 3–6 bedrooms, turnkey or light-renovation, current nightly rate within ±20% of comp-set median, title clean. Every MTR candidate still moves through the same per-property underwriting gate before acquisition clears: Per-property model: acquisition price, set-up capex, 5-year ADR / occupancy projection, opex stack, exit cap rate. Acquisition clears only if 7-year IRR ≥ 14% under base case.

Source: caribbean-presets.CARIBBEAN_JAMAICA_PROFILE.yieldBenchmarks[0] (TropicBay target band 8–12% net, USD-denominated) · caribbean-presets.CARIBBEAN_JAMAICA_PROFILE.marketMaturity[0] (~75% occupancy on managed STR stock) · investor-deck.INVESTOR_DECK.slides[acquisition].rows[Deal-flow criteria] · investor-deck.INVESTOR_DECK.slides[acquisition].rows[Underwriting] (7-year IRR ≥ 14% gate)

Caribbean pilot recommendation

Jamaica first, British Virgin Islands queued — on the existing operator pipeline.

The pilot recommendation re-uses the same founder-sourced acquisition stack the Jamaica thesis lays out, on the same Reg D / Reg S foreign-LP pathway. Jamaica anchors the 2026 launch; British Virgin Islands remains queued. The 8–12% modelled Caribbean band and the 6–8%modelled US leg for off-season stabilization track the ROI calculator's seed exactly.

03 · Jamaica → British Virgin Islands pilot lane
Caribbean pilot

Caribbean pilot recommendation — Jamaica first, British Virgin Islands queued

Pilot expansion. Jamaica launching 2026 with founder and family ties on the ground, USD-denominated yield target 8–12%. The BVI leg is queued second priority, with no committed launch date yet. Jamaica launching 2026. USD-denominated single-LP equity target 8–12%. Founder + family ties on the ground. The pilot lane inherits the same five-stage diligence sequence the deck publishes — Title search, building & land-use compliance, short-term-rental permit status, HOA / community rules, insurance feasibility, and property-condition survey. — plus the existing tropicbay-caribbean-… tag scheme that keeps 2 Caribbean rows grouped on the deal-desk. British Virgin Islands queued as second-priority leg. Acquisition pipeline open; no committed launch date yet. No committed MTR launch date is published for the queued leg. Illustrative annual net yield band after management fees, platform fees, and a vacancy reserve. Yields projected, not guaranteed.

Source: caribbean-presets.CARIBBEAN_PILLARS[01] (Jamaica launching 2026) · caribbean-presets.CARIBBEAN_COUNTRIES[0] (Jamaica pilot_2026) · caribbean-presets.CARIBBEAN_COUNTRIES[1] (British Virgin Islands queued) · caribbean-presets.CARIBBEAN_FUND_TAG_PREFIX (tropicbay-caribbean) · investor-deck.INVESTOR_DECK.slides[acquisition].rows[Due-diligence checklist]

04 · LP gateway
LP gateway

LP gateway — fractional slot or single-LP equity, same operator

Capital deploys into the MTR pilot through the existing surfaces the deck publishes: fractional slots at the published minimum-ticket band, or single-LP equity on the per-property vehicle. Single-LP equity tickets. Larger commitments welcome; capital is pooled per property for diversification across the portfolio. 15% management fee on gross revenue, no acquisition fee, no promote above hurdle — promote is negotiable per LP. Foreign-investor capital deploys on the same Reg D + Reg S structure that governs the Jamaica thesis leg — US LPs under Reg D, non-US LPs under Reg S where applicable, every per-LP operating agreement reviewed by US counsel and local counsel in Jamaica. The MTR pilot does not introduce a new fund vehicle — it is a stay-length positioning inside the existing Caribbean currency block.

Source: investor-deck.INVESTOR_DECK.terms.minimumTicketCopy ($100K single-LP / fractional) · investor-deck.INVESTOR_DECK.slides[returns].rows[Fee structure] (15% management fee, no acquisition fee, no promote above hurdle) · investor-risks.INVESTOR_FEARS[06] (Reg D + Reg S) · caribbean-presets.CARIBBEAN_ANCHOR_COUNTRY (Jamaica)

Walk the MTR thesis into the operator

Walk the MTR thesis into the deck, the model, and then a founder call.

The MTR pilot lands on the existing fractional and single-LP surfaces — same Reg D / Reg S pathway, same founder-sourced acquisition stack, same 8–12% modelled Caribbean band. The fractional surface unlocks the shorter ticket; the /invest surface walks the single-LP capital partner through the per-property model and the term-sheet template.

Read the deck (PDF)Talk to a founder about mid-term rentals
Read the fractional thesis →Walk the /invest hub →