Keep it simple Sounds like LLCs are overrated.  

My last years accountant made it sound like filing by myself would be easy this year as sole owner but I’m stumped on which forms my father and I need to file. 

Wow man sounds like I literally just read my bio.

Sounds like you got a winner there :) We actually just bought a new one last year- amazing location with main house on a great corner, and separately addressed guest house in the back that we rent out.

@Sarita Scherpereel you sound amazing!

I hope your ARV is more than $1.2, but it sounds like you want to use this as a short-term rental. 

@Carlos Ptriawanjust because a person has the letters CPA after their name does not mean they are giving sound financial advice.

I am sure if you were going to install a couple of windows they would give the homeowner a permit to do that, but it sounds like you are doing quite a bit more work.Every city and county is a little different.

I just wouldn't cover an unlicensed welder. the guy who you are covering for is the problem. or have him get insurance you can get one time policies. it just sounds complicated I'd pass on deals like this to make a few bucks not worth it 

Reading between the lines it doesn't sound like you have a lot of passion for being a housing provider so why not sell it as is before you put any more money into it?