If this was your first year getting a 1099, then there might be a small chance that you could get away with just this year's 1099.....HOWEVER, since you have been 1099'd for 2 years now, then the mortgage lender may request tax returns before extending a mortgage. 

Sellers did not allow us to get professionals in to give estimates for a french drain before closing (yes, our red flag we should have walked away with), but agreed to lower closing price.

FHA has the self sufficiency test which also makes 4 units more valuable because you have a better chance of pass the SS test with 4 units versus 3 units. 2 units doesn't require the SS test so buyers also tend to like that inventory for FHA so they can avoid the SS test. 

There is a chance they will say just to send them the P&L from your property manager and the expenses that you also paid and completely ignore the rest of your books so it doesn't matter. 

There's a very good chance the issue(s) you face have already been discussed and answered.Go to BUILD YOUR TEAM at the top of your screen, and you can search for other MEMBERS or LOCAL MEETUPS.

- is there a chance that what my CPA meant, writing off the old roof at current depreciated value? 

There's a very good chance the issue(s) you face have already been discussed and answered.Ask questions in the appropriate forum.

This includes finding and vetting vendors, following up on estimates and completed work, and making sure turnover is as quick and painless as possible.  

Just so i can do the preliminary analysis on the propertySecond: I'm finding it difficult to get a clear price estimate of the CapEx's that might be needed.

Changing the name allows you to retain all the current accounts and credit history while ensuring the LLC reflects your new purpose.If you're concerned about privacy, consider changing the name while also updating any public records to reduce the chance of someone tracing the LLC back to its original purpose.