I also may be interested in putting a tiny home on it and renting it out.

Fred,You can rent your property on places like VRBO or others if the property is in Sarasota. 

I haven't set specific targets beyond this initial goal, but I may aim to increase my passive income to $5,000 or $10,000 per month in the future.Current PropertiesI currently have two properties:The Loft:This property is rented out long-term and generates around $300 per month in passive income after HOA and management fees.The loft has approximately $100,000 in equity.The House:This is a brand-new build (2024) that I'm currently occupying through house hacking.I invested $70,000 in the property, which means I have $70,000 in equity.My plan is to convert this property into an Airbnb or long-term rental within the next two years.Short-term rental comps suggest I can earn around $3,500-$4,000 per month, while long-term rental comps indicate I can earn around $3,000-$3,300 per month.Seeking AdviceGiven my upcoming financial situation, I'm seeking advice on the best course of action.

All in all I have broke even between rents and mortgage and repairs but the property has gone up about $100k in value.

Can they prove how long it takes to rent a vacant property?

You also have to consider loan amounts typically need to be above $250K will carry a 3-5 year prepayment penalty.The biggest thing I see is loan officer are quick to offer a pre-approval for you but the fail to run the DSCR/Rents ratios up front.

Plus every time the house sells you start that amortization schedule over and you're on the "winning" side of the payments from the new owner so to speak.Obviously this only works when you've got low payments yourself or you manage to increase the value of the home significantly, but is there anything else I should be looking out for here? 

If they aren't too bad, can use the money to get a mortgage, rent a room in your house and use that income to pay down the student loan, you may want to think about it.

Also looking for distressed properties to fix/flip or fix/rent.  

@Chiane Martin the biggest challenge to doing Boarding Houses successfully is investing the required extra time.LTR - take the least amount of time, but time required increases as you go from Class A, to B, to C, to D.MTR - take more time than LTRSTR - take more time than MTRBoarding House - can take an insane amount of time to manage!