My overall goal is to generate monthly cash flow, and my current property might be a better rental option since it has equity.I’m also considering starting a business and purchasing the next property in the business’s name.

Is one better over the other or do you just get the data from the source directly (gov pages)?

Weirdly, you may actually be able to get better terms and/or more LTV on the refinance if there is debt on the property as lenders have rules for max cash in hand (max proceeds you get at closing) for cash-out refinances.  

I'd build up and go for at least 2 units but 3 stories is better. 3 story walk up apartments account for almost 65% of apartment developments round he country. this is what I'd recommend on your lot. this is 35' tall and we do it in columbus oh 

I bought several multi-family this way and negotiated financing terms that were better than the bank.Cody Davis started investing at 19.

Quote from @Gregory Wilson:As for the second, there are only about 20 monetary numbers to be entered in Turbo Tax on a single unit rental property 1065 so it always seems to me that the $3500 would be better spent elsewhere.

Quote from @Shiloh Lundahl: This mistake is in thinking one can time the market. 2012 was a better time to invest than 2019, and 2019 was better than 2024.

I find that it produces better returns and work great to trade up and accelerate wealth building. 

Quote from @Brandon Robertson Quote from @Denise Evans: Do NOT sit by and let him build and then hit him up for a "better price."

In your case, you are probably better off buying a break-even deal in Tampa then a deal with $200 cash flow OOS.