This is going to be my first home purchase so I want to ensure I have everything correct before making my first big investment.

Ensuring that GC's are showing up, getting ample work done in a timely manner, and working according to your expected quality is important, but you may run in to red tape with the city and/or utility companies as well.

I have no problem extending it early but I would check to ensure it's up to market rate, or close to it.

I agree with the above - if you've done your research but you need to take the next step with investigating properties - then your best bet is to ensure you have your lender/financing available and then contact a realtor, preferably in the REI market, who can assist with navigating your market of interest and help find the property types that will work with your ROI model.Typically, your realtor is you best asset who can point you in the right direction as far as contractors (make sure they're licensed and insured).

I want to move toward immediate eviction, but I want to a) avoid more property damage (unlikely), b) ensure I am prepared with any/everything I could need to file for eviction. 

Ensure you properly calculate all holding costs.

I believe the original lessee will be required to pay his fair share up until the point that a new roommate takes over I'm just not sure how to go about ensuring this gets enforced.

Whenever you are buying a property out of state you should do a few things to ensure it's as smooth as possible.Don't buy in the roughest neighborhood in the urban core.

., ensure the loan period term is much longer than anticipated hold period, DSCR must be at a certain minimum level), but it's still a much bigger consideration than with small multis which have 30 year amort periods.Lane Kawaoka, congrats on your latest syndication which utilizes 30+ year HUD loan.

@Nicole BlairIf you have a contract that protects ensures seller performance then you are protected by with whatever you decide to send him.