I would not think that the style of roof would dictate loan terms.

That might be on the property management company that he was using but it appears that he has had knowledge of it for some time and continued to promote selling more properties to be managed by the same property management company.

I would continue inspecting to ensure compliance. 

This is why California is bankrupt now and why the state continues to lose population.How about this solution?

I’m looking to continue to invest in CT as well as learn the markets in MA so I can start finding some deals around here.

In addition, the market dynamics make it seem like continued rent appreciation over the next few years is very likely. 

With the new job I don't really have time to continue to renovate the apartments and I don't have the money to hire someone to renovate them right now either. 

Give the tenants deposit slips and they can deposit the rent at the bank where you don't have to worry about receipts, robberies, or whiny tenants giving you a laundry list of maintenance issues.If you do continue receiving at your office, I recommend a security camera.As a business owner, I would probably file a report with the police and notify the tenant I will not be renewing her lease.

If I believe they have taken steps to improve their situation, and I am comfortable they will continue to do so, I will often request something to mitigate my risk and move forward anyway. 

Following this "Rule", you will never need any more money from other sources, since you will continuously be supplying your own...at will.Use your seed money, spend your profits...after, you've reinvested your initial profits to expand the original seed money.