Should I get a traditional mortgage and take cash out, or a HELOC on this property.I have a long term tenant already whose lease payment can pay down the mortgage/HELOC.  

2️⃣ Do older duplexes in this area typically perform well long term if systems are updated?

For those who done this for a while:How long does it typically take you to fully analyze a deal?

I’ve been in property operations and management for about 5 years and currently serve as a Regional Property Manager overseeing both long-term and short-term rental portfolios.On the long-term side, I support two ownership groups and oversee day-to-day operations across 15 multifamily properties totaling 270+ apartment homes.

Hi everyone — I currently manage a small-to-medium sized rental portfolio that includes both short-term and long-term units, and I’m looking to optimize my tech stack.

Even with all that growth, you can still find properties around the $120k–180k range that hit the 1% rule and produce positive cash flow, which is why many out of state investors are targeting the area for long term rentals with strong appreciation potential as well.

I’m always looking for solid assets in good locations where there’s room to improve the rents and hold long term.A good example is a deal I picked up at 1927 NW 20 Ave in Miami.

Inherited a 3/2 single-family property in rural Mississippi that is approximately 90% complete.Remaining work: ~ $20,000Back property taxes: ~ $6,500Family loan ($10,000) can be repaid at closingEstimated finished value: realistically $120,000–$140,000 (not assuming top-end pricing).We believe we would need approximately $25,000–$30,000 to finish the property cleanly and list it for sale, though we are pressure-testing that assumption.Challenge:• Thin credit file on my end (695 score, limited history)• Husband has income but prior negative credit history• Seasonal and variable income (no stable W2 employment)• We cannot support required monthly loan paymentsWe are specifically trying to determine whether a short-term loan (6–12 months), secured by the property, with interest-only or accrued interest payable at closing, is realistic in this scenario.Questions for experienced investors:Are loans structured with accrued interest (paid entirely at closing) realistic for a borrower profile like this?

Appreciation on this house in this area will play a huge role long term.

Hi there, has anyone transferred ownership of a property already registered with Chicago for short term rentals to an LLC?