You definitely wont get an app like that for free, so how much would you be willing to pay to a company to submit it for you, vs spending 10 minutes once a month to submit taxes? 

My cost wont necessarily be the same or comparable as I GC my own projects and have trade skills.

He is very good about deductions on tax returns so his income looks negligible and of course banks wont talk to him about loans.

If I put all of my eggs in one basket (Florida in this case), paid off property and a hurricane blows everything away, FEMA is nowhere to be found and the insurance companies take years to pay what little claims they actually do pay, I suffer through it in a blown out house.

the other reason wholesalers wont get licensed is the guru's tell them they don't need it and its legal in very state ( which it is not) and the reasons you don't want a license are as I mentioned the fiduciary laws.. 

Finding contractors in Florida after 2 hurricanes wont be easy or inexpensive 

I have not done much work to my personal home in Hollister since it wont make me any money in the short term.

I wont need to spend that money now.   

Knowing which subs go deer hunting , fishing , will or wont work weekends , which ones are tied up on longer jobs , etc .

If you're a newer investor, unsecured private funds will most likely be your best option, however it wont work for a simple buy and hold.