LLCs  have expenses associated with them (which depending on the state can include annual filing expenses, and filing fees for holding properties in other states, etc), but for just getting started or owning a small number of properties , you likely do just as well to just have some extra umbrella liability insurance.  

If either of these options sound appealing, it's better to consult professionals for a fee so that they can provide guidance on any legal issues or liability concerns associated with owning rental properties without investing any capital yourself.

I would set a year built filter with your other criteria and see what it returns...remove the filter and see if the properties showing are something you can be comfortable with.It's more important to focus on the location and configuration of the property and opportunity for value add than focusing on year built.That said, older properties (if not updated) will always require more work to get stable due to inherent issues associated with the building style and materials...stone foundation, slate roof, balloon framing, ungrounded or unsafe electric, and possible abatement of hazardous materials...

So the bottom line is when people have shown they make bad decisions, the government needs to step in and make their decisions for them.As far as the other red tape associated with Section 8, that is to protect tenants and tax payer money from dishonest landlords.

The only way I've ever been able to permanently resolve this issue is to remove the tenant associated with the guest. 

Just do a search on the forums (or Google) and you will find out that there are lots of fine print details associated with your description.

Get yourself to a Real Estate Investors Association meeting.  

Get the as is value, a quick lipstick upgrade value with associated costs to do so, and a value after complete rehab to full retail value along with those associated costs.

If you have a good CMA, and the numbers make sense for you then the last question is whether you have the liquidity to cover the costs of a low appraisal and to what degree.

Something you may want to do is compare some of the other costs associated with rentals.