They still run your credit and you can absolutely be denied for poor credit, but it's a much more open process.

Painting, cleaning up, etc - stuff that takes a lot of time but doesn't require specialized skills, and even if done poorly would not cause serious damage.

Get rid of any bad tenants right away, the good tenants will appreciate this and will want to stay.Training poor inherited tenants can however be challenging if the previous owner did a poor job of enforcing the lease, often it is easier to start with new tenants from scratch.

Your best bet is measure each room and add up your actual square footage.

I think it's generally poor judgment to post this sort of thing. 

This leads to my question - should stay with this current PM for the eviction process (which I'm told takes about 3-4 weeks) but risk them handling it poorly (is it possible to mess up an eviction?).

Living in the property I only need to put a 5% down (I am young and very poor so this would practically be my only option)2.

Just listen to the sales pitches by the hundreds of different companies that sell health insurance and every company had so many options for health plans the average person cannot remember more than 10% of what a health insurance salesman tells them and I will bet money on that because I know for a fact that when sitting with health insurance salesman no normal person can remember and compare all the different plans without looking at the charts, brochures, schedules, different co-pay plans and then compare the benefits and cost for PPO vs, HMO and my list can go on forever.

I just don't know if it is worth it.Is it likely I will recoup any investment to address some of the fundamental issues (raise sagging floors in the lower unit plus addressing issues that will cause in the upper unit when the walls raise 1-2", replace galvanized piping, re-do the poorly done roof) when we look to sell in 10-15 years?

Cash out refi will be the best bet if it's going to be long term debt that you pay back over years, HELOC will be best bet if you're going to pay it off quickly.