I have a running list of the issues that need to be fixed and can't spend anymore of my free time tackling them. 

I would proactively tackle small tasks that could lead to bigger costs down the road such as checking traps, filters, small leaks, ect.

But alas, the reason for my post; currently my biggest barrier in tackling the move...Where do I live while I search for & close on my next home?

As for tackling smoke the best courses of action are washing walls before painting, then prime and paint. 

This will provide an opportunity to learn the process, get copies of all the documents they use, and help you decide whether you want to tackle it on your own in the future.I recommend you call around and try to find an attorney that specializes in evictions or at least has a lot of experience with them.

I'm trying to strike a balance of trying to tackle problems that arrive and not just back out because it's different or scary, and recognizing when it's not a deal I'm willing to do.Any tips, advice or encouragement?!

@Daniel OhI'm in the same situation as you brother,My suggestion (If you're really serious about investing), would be to look into wholesaling or house flipping to start building up some capital and rapport first before tackling rentals.

I say all that to say, maybe let him know your frustrations and work together to figure out your goals and then based on your goals you can back in to what strategy you should tackle. 

I have an opportunity to convert a 7 room boarding house into a rental property.Have you tackled a project like this?

Glad to be tackling on a project with him--very knowledgeable active duty real estate investor and Blackhawk pilot.