It's easy to mess that up by not digging deep enough, putting in proper rock and possibly tying to a drain tile (easier said than done), oh and sealing the new hole in foundation properly. 

I haven't been able to dig really deep to see if there are any next of kin, but I'm assuming that's where I need to start. 

Expenses on a SFH generally run in the range of 50% so with only $100 over mortgage payments you will be deep into negative cash flow.

You need deep pockets to ride out the major expenses along with supplementing your rental income to pay the bills but that is the way is seems to be out there.

Depending how deep this is it can cost a few grand. 5.

All we care about is are we getting the property at a deep enough discount that we can make money.  

This is why the DST, TIC or a stand alone NNN property of your own make sense combined with the 1031.And while you're absolutely right to look deep at the actual costs and fees both entering and exiting a DST or a TIC project you can find cost effective quality returns that will rival or beat the stock market average - especially if you factor in tax savings and ongoing depreciation.The age old question on pay the tax now or pay the tax later can best be put into perspective running numbers. 

I’m taking all of your advice into deep consideration as I try to figure out what direction to go in.

It could take up to 10 years or more to grow to the point of having significant enough income to replace a paycheck.If you want to flip you could be facing some very lean times without a job to support you or you would need deep pockets.High paying consistent long term employment is the easiest way to successfully invest.

There's a fear that if you jump into the deep end there's the possibility of drowning.