Some local lenders familiar with Gainesville’s market (from what I’ve read in Bloomberg) like SunState Federal Credit Union and Ameris Bank have been mentioned favorably latley and might be a bit more flexible if they understand the repositioning story behind your property.

Check "flexible" dates for a house with a pool to weed out the condos with shared pools.

Simplified ManagementFor those managing multiple properties, AB 2622 streamlines operations by expanding your hiring pool and removing the red tape often associated with minor repairs.Why It Matters for TenantsTenants also benefit from AB 2622:Faster Maintenance: Minor issues like plumbing or lighting can now be resolved promptly.Fairer Move-Out Costs: Affordable repairs mean tenants aren’t hit with inflated charges for damage beyond normal wear and tear.Things to Keep in MindWhile AB 2622 makes maintenance easier, landlords should still vet unlicensed workers carefully, ensure proper insurance coverage, and remember that jobs requiring permits must involve licensed contractors.AB 2622: A Win-Win for California’s Rental MarketAB 2622 strikes a balance between flexibility and accountability, making it easier for landlords to maintain high-quality rentals while fostering better tenant relationships.

I’d suggest starting with local credit unions or community banks—they’re often more flexible with investment properties.

Is it better to pay cash or leverage my liquidity to maximize ROI while retaining flexibility?

.* Property in a flexible market to switch the rental from an STR to LTR (if STR doesn’t work out).Questions:* What are the prospective neighborhoods or areas within and around Houston for STR investments?

As Pat mentioned you have a lot more flexibility with home 1 because it has no mortgage and is not owner occupied.

@Josh OteroThe hardest part for me was being flexible with my tenants and realizing all these people are living paycheck to paycheck.

Electric: is the easiest to split, but may require holes cut in walls to separate the units.Gas: gas lines aren't as flexible as wires, but it can usually be done affordably.Water: most cities will NOT install additional water meters on a property.

As already mentioned, he wouldn't be able to use rent from roommates to help qualify but based on the numbers you shared there should be a VA option available considering how much flexibility there is.