How I got started is easy: I saved all my money, hustled up income everywhere I could, didn't spend extravagantly on consumer goods, went to college, got a better paying job, saved more money, learned how to do/fix/install virtually everything. 

I am in the same field, and I got into real estate and think it works fairly well with education (if your job has some flexibility like mine)...I can recall spending like a hundred grueling hours fighting over half someone's deposit in the legal aid office and stalling the eviction an extra week or two on  technicalities (a noble cause for sure), but they still, of course, were evicted eventually with no money.

If they were in a higher bracket I would spend a bit more time with it though. 

I will also be financing, does not need to be single family, I am open to other properties, such as apartments, but if an apartment, can't spend  more than $140,000 since I am looking to avoid PMI and would like to put down the 25% required to avoid this.

Then they fail there occupancy inspection and end up selling the property for a loss or spending 40K to fix everything.

Aside from that, I am very diligent about paying myself first and making all cash savings/investments come before any bill, monthly expense, discretionary spending...etc. 

Obviously there comes a time to do a full replacement (you don't want to risk a major leak/damage to the interior), but if you can spend $500 now and get another 5 years out of the roof as is, that might be a good business decision. 

I never made any money (cash flow) from this property for the past 8 years except  spending money for different expenses and repairs (due to a bad renter and age of the townhouse).

If you allow him to bid a job instead of by the hour, you might spend a little more, but you will know beforehand how much it will cost and he will have allowed himself a little extra $$$ to allow for variables. 

They'll pass your name on to the buyer (who probably already has his own contractor).If a contractor will agree to run out and spend a few hours on a make-ready estimate for a new investor he's never met, that's actually a red flag about the contractor.Start with the books.