One of the largest competencies of REI is scalability through other people's time (OPT), often times carried out through PMs.If your goal is to own a smaller portfolio, then perhaps doing your own property management makes sense.If you want to acquire medium to large scale apartment buildings, then you probably won't even get a loan from a commercial bank without proof of using a PM with a solid reputation.

But.... don't get carried away.

Usually higher returns carry much higher risk.

I've only come across a couple 401k plans that allow you to carry the loan and continue making payments after you're no longer employed with that same employer.If you don't repay the loan, then it's counted as an early distribution.

Make sure that you have all your notes, pictures, work orders reports etc...keeep copious notes, its one of the most important items.

If this isn't a separate dwelling unit you can't take losses from the rooms / space you are renting and use them to offset non-passive income (Section 280A of the tax code)Rental expenses are limited to the amount of your rental income and the balance of rental expenses is carried forward. 

@Nate PucelThis will get answered based on the contract you have with the roofer and possibly your insuranceTypically a contractor is not responsible for consequential damages - meaning if they break something they are responsible for that item, not for any lost revenues etc.Now your insurance may have rental loss on it and they could go after the insurance of contractor but that also depends on your type of insuranceSo the answer is : it depends on what the agreements are

The new property is the tax shelter that can take some of the burden off of your carry over year to absorb some deductions.

There are not any unsafe items that MUST be repaired. 

One additional item is that I am planning to move out of my current residence no matter what, so will need to rent/buy for that.