This could get quite tedious depending on the search capabilities of the county.  

At some point, I almost wonder whether its worth fighting that though.These HOAs can regulate a lot of stuff and they tend to think they can do anything they want.

Is he capable of building equity through rehab savings?

A smaller slice of something is better than a larger potential slice of something that doesn't exist.When I get inquiries from investors on the commercial side my number one factor is " Do they have the capability to buy and are they realistic for market conditions where they want to purchase?

Of course it makes us uncomfortable as we are not sure what else he may be capable of doing.

The project is quite simple and will take less than a month (mainly cosmetic).The seller disagreed with the entire rent strategy from the get go and basically told me (in private) that she doesn't want them to pay under market value rent b/c they've lived free for almost a year, and at $800/mo, I won't be able to get them out without a fight. 

The upstairs unit had a break in and what appears to be remnants of a dog fighting trainer so the upstairs unit would definitely need some more work.  

I wish I had more knowledge to offer you on this particular investment, but I'm not too familiar with what kinds of returns turnkeys are capable of generating.

Of course the increase return goes along with the increase risk.If you invest in a real estate equity fund which has multiple properties in different states, you will receive a consolidated state k-1 for each state the fund properties are located not at an individual property level which helps with the paperwork.Also there are new funds that are offering 1031 capabilities say some of CrowdStreet and RealtyMogul but the minimums for that is quite steep at $100k which guess makes sense since you need significant capital to make sure you can go and buy/acquire the next property for the 1031 exchange.Good luck!

I would suggest that most of these are not for the new investor - unless your day job is a trade - and are probably best for a local investor (or at least partner) who knows the lay of the land.As an example, you will find $30K - $80K houses, and multi-units, in Saint John, but an address difference of 1-block can be the difference between a fighting chance and a nightmare.