I plan to live in it while we renovate to avoid the float costs. 

For long term, this is a perfect home and I don't mind living here for a while and it's one I can have my parents live in as well due to it's convenient location, so I don't mind having it as a buy and hold/short term rental combo but I'm scared of the foundation aspects because I don't really understand the scope of what this means. 

If your number of assets is getting larger you may want to have a discussion with the attorney about an estate planning aspect, for example it may make sense to have ownership of the properties in some kind of trust, but if you don't have many assets (or dependents) then maybe it's premature at this point.As far as filing to create the LLC, my usual advice is, if this is your first time, use an attorney and pay attention to what s/he does.

He charge a monthly fee for this client for bookkeeping as well as some aspects of property management, i.e. walking checks to the bank.Back before ObamaCare, I was paying $1,500/month family health insurance which I cannot easily deduct off my schedule E.

I already do that in various aspects in life - helping others without expecting anything in return.

Reason i'm asking is if I pay all cash, I can get 80/20 Cash out Refi with no seasoning in a commercial aspect through my business but if done on a personal basis, that seasoning of 6-12 Months follows Fannie and Freddie's guidelines.Has anyone else done this before? 

Longevity and durability are key, but don't overlook spending a few bucks now to avoid big ones later. 

However, you should make an offer, get it under contract, get an inspection done, which will likely cost a few hundred bucks, but a small price to pay for locking down a good deal, and also a small price to pay for avoiding a major headache.

Also, longshot, but anyway to avoid paying the transfer taxes and recording fees twice in that instance? 

We finally found him an off market deal through our friend network, thankfully, hard to avoid overpaying when your competition is coming in multiple six figures over asking, cash, no contingencies, no appraisal, no inspection even (also becoming common here).