By Eli Sanderlin · April 25, 2026 · 10 min read

The Coastal Florida Investor Playbook: Acquisition, Hold, & Exit Financing

Real estate investing isn't one loan — it's a stack. Here's how I structure financing across the lifecycle of a coastal Florida investment, from offer to exit.

Stage 1: The acquisition

Goal: close fast, lock in price. Three financing modes:

Cash-equivalent close (DSCR with 21-day commitment)

For competitive offers. DSCR loan lender issues commitment within 14 days, closes in 21. Submit a "subject to financing" letter that reads like cash. I have lenders that consistently deliver this timeline.

Bridge loan

9–24 month interest-only term. 80–85% LTC. Used when: you need to act faster than DSCR allows, the property isn't yet rentable (renovation needed), or you're in a 1031 exchange deadline.

Hard money

7–14 day close. 70–80% LTC. Asset-based — minimal income docs. Cost: 9–13% rate plus 2–4 points. Use only when speed is worth more than rate (which it often is).

Stage 2: The hold (refinance to long-term)

After acquisition / renovation / leasing, refinance into long-term DSCR or conforming.

DSCR refi (90 days seasoning typical)

Most DSCR lenders want 90 days seasoning post-bridge close. Some allow "delayed financing" with no seasoning if you bought all-cash.

Conforming investor refi

Up to 10 financed properties on Fannie Mae for individuals (more on the second mortgagee theory). Better rate than DSCR, but full-doc and tax-return scrutiny.

Portfolio refi (5–50 properties cross-collateralized)

Single loan secured by multiple properties. Streamlines servicing. Common for serious operators with 10+ doors.

Stage 3: The exit

Three primary exit strategies:

Sell + 1031 exchange

Defer cap gains by buying replacement property within 180 days. Need a qualified intermediary. Bridge financing on the replacement is often used to close before tax-deferred funds arrive.

Cash-out refi to extract equity

Pull 70–75% of new appraised value as cash, keep the property, redeploy capital. The "infinite returns" play if the property has appreciated significantly.

Outright sale

If insurance or regulatory risk has shifted (think: STR ordinance change in your jurisdiction), sometimes liquidating is the right call. We model the after-tax exit before the listing.

The 5-property coastal Florida portfolio template

Here's a real structure I've helped clients build:

Property 1: Florida Keys STR, $850k, 25% down DSCR, ~1.25 DSCR. Cash flow $1,200/mo.
Property 2: Treasure Coast LTR, $425k, 20% down conforming. Cash flow $300/mo, building equity.
Property 3: Cudjoe Key STR, $1.1M, 30% down DSCR, ~1.30 DSCR. Cash flow $2,400/mo.
Property 4: Naples condo, $675k, 25% down conforming investor. Cash flow $400/mo.
Property 5: Marathon STR, $1.4M, 35% down DSCR (insurance-heavy property), ~1.18 DSCR. Cash flow $2,000/mo.

Total deployed equity: ~$1.2M. Total monthly cash flow: ~$6,300. Equity build through principal paydown + appreciation: ~$300k/yr.

Common mistakes I see investors make

Treating each property as a standalone deal instead of a portfolio strategy.
Failing to model insurance escalation (5–8% per year coastal).
Buying with a strategy that doesn't survive a hurricane year (need 3–6 months of full PITI in reserves per property).
Cross-collateralizing too early — losing flexibility for future refi.
Not optimizing entity structure — LLCs vs personal — for liability and tax.

Bring me your portfolio

If you're 1–10 doors deep in coastal Florida and want a strategy session on how to structure your next 5 acquisitions, book a call. We'll map the financing stack from acquisition through exit.

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