Listen to the song ‘Vienna’ by billy Joel.

If more, you should capitalize.If you forgo the DMSH and instead apply the BAR tests, what you're describing would almost certainly be betterments and therefore an improvements (read: capitalized). 

@Alex F.Banks want certainty of closing and is willing to forgo some price in exchange.

You can transfer the property into the LLC but also want to chat with your lender about any ramifications for going that route as well.  

Knowing these students aren't going to have much credit/income yet (and they're freshmen so doubtful they've ever been evicted), would you forgo the screening on the tenants and only have the parent/guarantors pay the screening fee?

Not unlike the infamous Eagles song, Hotel California, you can join but you can never leave.

@David Song By two person LLC I mean having myself as a 99.9% interest owner and someone else as a 0.01% owner, similar to what Philip wrote about in his insightful blog post.

Like paying them a property management fee or work some kind of payment deal for going to view the prooerties for me and talking with contractors.

But you don’t get much of a discount for going that far out of town like you used too. 

Recently I saw a video where a wholesaler was saying that the lot size has to be within 2500 sqft, im just curious if that applies for going over 2500 or under 2500.