The contract with the wholesaler also expires on Monday the 27th, so I have my concerns about this just being a stall tactic to get out of the contract.

Typically those purchasing cash aren't inspecting every home, they're walking it or having their go to GC walk it and already know what they see that may be a concern. 

I’m wondering what all I need to provide my tenants with this year as far as taxes are concerned.

THEN, I plan to purchase the second home using a FHA or conventional loan (3%-5% down), for which I will likely pay the monthly cost out-of-pocket, maybe with some rental income support if it is a duplex.My concern is, I do not want to spend my savings or weigh down my debt-to-income ratio so much so that I cannot qualify for and pay the down payment and closing for the lending on the second home.Questions: - With the first home being multi-family, 75% of the rental income (or potential rental income initially) will relatively either maintain or boost my debt-to-income ratio from lenders' perspectives, right? 

Some have done owner financing with an agreement to pay all interest and equity splits when the home sells others have done it where they do a quitclaim adding their name onto title with the seller so once rehab is done the seller can't try and cut you out of the deal. 

A HELOC comes with a variable interest rate and all signs are pointing to no further Fed rate cuts in 2025 - and there may even be rate increases.- So, you may want to consider locking in an interest rate via a 2nd mortgage.Do you have reserves for unexpected expenses?

Thanks in advance.Hey Cosmo,I do think there is a growing concern towards the reliability with section 8 with varying administrations right now.

Mortar, paint & bonding materials deteriorate leaving cracks, gaps, etc. which can be concerning to look at, but this is very often addressed with repointing.

Just personally, I would never do an absentee landlord kinda thing....Too many moving parts, too much to go wrong and cuts into your profit big-time....Sentimental value is one thing, but not if you end up hating the house down the road.....Stay local, plenty of opportunities in good ole AZ.....

We have zero concerns of squatter in SWFL.