.- Should I engage an attorney to prepare for lawsuit?

You may want to consider working with your tax strategist remotely to expand your options.I would also recommend looking for a tax strategist willing to work with you throughout the year, not just when preparing your tax return.

This would allow you to get some cash out, make the final repairs, and then do the final cash out refinance to prepare for your next one.Good luck!

True, it is way cheaper than having it professionally done, but just be prepared for the whole process to go at a snail's pace.Wes

Any other advice on how to prepare for the inspection is welcome.

You will be be responsible for the transfer taxes equal to the assessed value, plus deed preparation fees and if there is already a loan, that adds another layer of complexity.

Every year, my CPA prepares my tax returns.

Or better yet, are you prepared to buy with a negative carry where that negative carry can grow in magnitude?

I value what you are offering; but I'm not prepared to pay $2000+$250/mth right now and go through this again. 

and seeking some wisdom for a rookie.Interested specifically in Kissimmee/Orlando/Davenport as Disney market feels familiar to me and it’s generally a cheaper entry point than beach condos.Looking at Regal Oaks (staying here now on vacation myself and enjoying it, though have read mixed things about occupancy), Windsor Hills, and Champions Gate.Goal is to have a second home that I AirBnb out the majority of the year but also can escape to when NYC is ruthless (like now :) hoping to live in the 150-250K range, bonus if there’s a pool (regal oaks has community pool and individual hot tubs), and solid amenities.Other than reading for my life, how can I number crunch and prepare for this?