This has already started to help as I pour through all the information on this site. 

I'd suggest using the calculators here on the site.

It has been a good a great experience for me and I am trying to convert some of my other properties to section 8.The tenants take good care of my houses because if they don't they get kicked out of the program and they lose their free money.Section 8 pays 110% of market rents also

However, would I lose my deposit if my lender refuses to lend prior to the 30 day period because the roof hasn't been fixed yet?

@Mindi Rosser & @Greg GerkenAs someone who does this work for a living, I can assure you, you do not want to get in the weeds with this stuff.Some investors spend way too much time getting the site up and running.

So, if I can add a 4th bedroom, without losing say a garage, for a reasonable cost, I can boost my value by $10k. 

I will not be living there, so house hacking is a grey area (essentially I would be lying about living on site if I went that direction).

@Alison P.Don’t lose any sleep over this .

Start studying as much information as you can about real estate investing on sites like BP, YouTube videos, etc. 

I checked the Better Business Bureau for complaints, I checked the NJ State Attorney General consumer division to ensure he was licensed, I checked every reference he gave by visiting sites and speaking with the homeowners.