I joined about a year ago and my life went to heck in a hand basket.

I now have a handful of properties here and, looking back 10 years, I wouldn't have done it differently.The reason is simple: in life, you need education.  

Are there any expenses that you could lower or boost income?

Hi @Adam WorthNote I'm not an expert negotiator but have been doing sales for a while now and since I'm still very young I'm noticing that the results you seek out of life comes down to how well you negotiate lol from buying a car, going on a date to everything (at least my experience lol) But this in one of the reasons I truly love Real Estate there's so much information out there for your disposal that you can justify the offer your going to make regardless the amount.Since he's your neighbor don't feel like you're going to insult him because you just never know what that person is going trough in closed doors a ridiculous offer just might make his day especially if he can't financially keep up with it or it's stressing the person out.Regardless just be prepared with facts baking up the offer your making, you can do this buy talking to a Realtor to get a CMA to see what has sold and get a ARV since his home is similar to yours, since you mentioned he overpaid this tells you that he might be underwater or have no equity this gives you an opportunity to ether lease option or some type of seller financing.

I bought my first property when I was much younger and it turned out to be one of the best "accidental" decisions I could have made in my young life.

I'm currently in the oilfield, and have been very successful in this avenue of my life.  

yup.)My biggest regret in (my financial) life was not  not picking up the homes that went into foreclosure in my neighborhood back in 2007-2008.  

You and your family will never be in want of something to do here.I have lived in the city of Philadelphia my entire life and have worked in the suburbs most of my adult working life. 

You might get at least an idea on how much life the roof has left in it, and how old your water heater is, HVAc, heating system, etc and figure out a number to set aside for replacing those someday. 

We have done very well self managing and investing in this crazy life ;)