I’m also considering advising my tenant to look into Section 8 assistance, as it could help support their financial situation while allowing me to adjust the rent closer to market levels.

You get your own dedicated customer service agent and she handles anything I need in a very fast response time.I have run into a couple issues in the buying/rehab process, but I will say REI has rectified the situation to my satisfaction every time and without major pushback. 

I'm just in a bit of a chicken-egg situation.

I have been in this situation before and having documentation to send Airbnb helped win my case.

Every investor  has a different risk tolerance, comes from a different financial situation and has different financial goals.

I’m self managing myself but the tax side of it is a little confusing to me but I’m recording everything involved as far as maintenance, traveling, expenses etc. just want to know what some people would do in my situation or what to I can benefit from come tax season  @Angelo LlamasI recommend that you find a real estate accountant to help you understand and prepare your taxes.Bigger Pockets is a great place to find a real estate tax accountant. 

Italy you can get loans for 3 to 4% but the properties have to comply or you have to correct if possible the situation.  

The tenant base is generally 95% single women with 2 to 5 kids and they flat destroy houses, Not on purpose  most of the time but if you have children all below 10 years old they are just brutual on houses even in the best of situations of which single parent with multiple baby daddys is not the best of circumstances.. full stop.

It's... not an ideal situation and we're kind of working our way through the grieving process.

buy and hold situation Lessons learned?