Focus on Cash Flow Early On:While appreciation is the long-term play, as a beginner, I'd recommend focusing on cash-flowing properties to provide you with a safety net and help you ride out any market fluctuations.

If you already have a solid team in place with your first property adding a second should be fairly easy.

He is 44, lives alone, has a landscaping business that is doing fairly well.  

But I'm still fairly new to MTR/STR so I'm learning as I go.

So it isn't a complete waste, you would simply need to follow the strict reading of the law with no private clauses for consideration...I'm not sure how that plays out since technically if the lease is void, so is the tenancy meaning you could terminate anytime and not wait for the original lease expiration...I'm sure that's covered somewhere, but again I'd ask my local atty what to do given this is such a locally specific issue. 

I personally dont know where title insurance comes into play with these either if your not recording a debt instrument and then getting a lenders Alta

If so, why not partner with someone else that can help you fund the deal, either 100% or have your money partner fund 20% and a commercial bank fund 80% then flip it and split the profits w/ your money partner at whatever split you all think is most fair? 

I'll then list my properties on the high end of whatever I think fair market rent is.

Per fair housing regulations, I can't answer this question. 

You could go into NJ (although the cost to play is high in Northern, but the rents can be very nice), or you could bypass and head into PA near Delaware Water Gap and get low taxes and good renter options.