This is the conundrum that every investor is in and the answer is that it's an issue.The way to work around it is to prepare your taxes for a couple of years without the "optional" items that you can declare. 

Depending on how long tenants stay, assuming the average of 2-3 years, cost is minimal but every 3-4 tennat turn over may require more extensive upgrading of many items.

After that, I sold my entire portfolio and went into mobile home investing.

Funds received from sellers, nonprofit or other organizations, including state and local government agencies, for down payment assistance grants cannot be used to reduce the required contribution.Funds paid for costs outside of closing, such as hazard insurance, taxes, application fees, and other items related to the purchase, are considered part of the homebuyer’s required contribution.

. , Is your schedule A itemize deduction going to be higher than standard deduction?

I've now sold off all of those at handsome profits. 

W2 just seems to be a naughty word on BP, but I'm not sold yet that a solid W2 job isn't a route that should be encouraged to those wanting to build a foundation for a RE business as a full time investor.

Does anyone have any advice on areas that should be of primary focus or items to caution against?   

Obviously, the home could be sold as the old sq ft and the investor/buyer can just go and permit it for the increased sq ft,  but I would think that the county automatically will go and assess the home as soon as it changes hands since this the county has probably seen this before. 

@Abel CurielAt the moment the only thing i’m Doing is checking online sites and see what homes are being sold by owner.