As a thought - you could have the lease require them to maintain the lawn and, if they don't, allow you to pay for a service and bill back the tenants. 

My experience is that people who buy these units do so at a considerable discount and basically have to wait for the tenant to die or break some kind of law such as subletting/Air BNB.Also rent controlled units generally have SIGNIFICANT deferred maintenance issues because there is no incentive to maintain them.

If I were you I would set some goals that I could work on while I maintained the job I had.

Also, you learn info such as where historic districts are etc, to avoid buying something that will have to be maintained within the historic preservation guidelines, (unless you want something historic to maintain). 

AN LLC has to be set up and maintained properly to have any benefit and by and large, statistically, most people are ill-informed on LLCs and do not run them in a way that actually gives them the protection they bought them for.

I agree on 1031 is the only true way this is a case if you DO NOT want to maintain an investment in real estate. 

It seems the odds are against you recouping your costs if you maintain it over a long enough period. 

Your personal accounts need to be kept absolutely separate from your business accounts if you establish and want to maintain a separate legal entity for your business.

Rentals are probably better, all things considered, but everyone has a different threshold for what they consider hassle and I think a lot of people who are getting into rentals think the hassle is going to be quite a bit less than it actually is.Appreciation is great too, but the way I look at it, that's when you get into the real skill work - finding stuff that will appreciate while maintaining an acceptable level of risk aversion.

The only effect that loosening these rules is going to have are less maintained houses being sold.