I would also recommend you reach out to your local county housing authority.

If you have this extremely valuable experience already under your belt owning 2 properties, why dish out a potential down payment for property number 3 over to a mentor or coach?

I am going to start a marketing campaign sending letters to potential sellers indicating that I would be interested in buying their home. 

I'm always looking to make more connections in the area so feel free to reach out to me at any time.

I will reach out to my city and hopefully get that approved here in the near future. 

You'll want to make sure you understand the K1/tax filing implications because if you own very small piece of let's say 10 properties in 10 different states you would potentially receive 10 K1s (one for each deal) and 'may' have tax filing requirements in 10 states. 

In the grand scheme of things, yes, you should eventually replace the windows so 1) They operate properly. 2) It doesn't turn away potential tenants or cause maintenance hassles when a new one moves in.3) Tenants have proper egress in case of an emergency (like fire).Now, windows are expensive, so you'll have to decide how much you're willing to spend, based on how much income the property is bringing in.

If you're interested in the market, reach out anytime, I'd be happy to talk with you! 

Bruce: Thank you very much for the recommendation, I reached out to Lonergan.

Also you need to figure out how you intend to cover inevitable property damage done by guests but there are plenty of solutions for that in the marketplace where guests pay a flat fee per reservation in lieu of a deposit and you get covered for an assortment of potential issues (bad checks, credit card chargebacks, fraud, personal property damage, etc.)