Ideally a site/software that pulls names and addresses from a database right into the letter text and on the envelope with a handwritten appearance.What's best and why?

First property I didn't spend much time in before renting, so there were some kinks to be worked out with the first few guests which resulting in lower than ideal ratings.

@Avery Manison Here is my "starting up" collection:Read ideal-vs-desperate-investor (http://greeneincome.com/index.php/2018/10/29/ideal-vs-desperate-investor/)Read Dave Ramsey book "The Total Money Makeover: Classic Edition: A Proven Plan for Financial Fitness." and complete the baby steps there.Read Scott Trench’s book “Set for Life.”Finish the school and get your degree - you'll need it later, especially if it's business management.Get a job first where you have W2 income.

Perhaps your offer was "good" but didn't quite match their objective.

Ideally a company you can grow within. 

We rented it out to friends of friends that want to eventually do a rent-to-own type of scenario, we don’t know if this is ideal for us though.

ideally you want to inspect every single unit in a multifamily..... when you are talking big numbers, that not practical, but you should try and inspect as many as possible and YOU get to ick the units and numbers.Believe it or not, there are sellers that will hide stuff from you :)And again on cost.... it really depends on how much water damage you actually have and what you are putting back in..... this isn't necessarily a "basic remodel"..... so don't compare it to just a "remodel"......

I'd simply ask for a breakdown of the charges and payments applied to the loan, since your accounting doesn't match his, and you'd like to reconcile now rather than later.  

I just hate that most of the people I deal with for business are so behind on technology.

In Milwaukee most of the quads we have are small units and affordable housing type properties; not really ideal for a house hack.