I enjoy video games (Destiny, NBA 2K19, Fortnite), Movies, TV and hanging out with friends over a drink or a cigar.

I like you did not have enough money to qualify for traditional lending.

If you're self-employed, the Solo 401k plan will likely work better for you.A few Solo 401k benefits: Compared to an IRA, Solo 401k contributions limits are roughly ten times higher.There is no custodial requirement for the 401k.The Solo 401k can allow you to borrow funds from the plan, unlike with IRAsYou don't need the additional expense and administration of an LLC to have checkbook control.There is a built in-Roth component whereas IRAs are either traditional or Roth, not both.A spouse can also participate in the same Solo 401k plan.The Solo 401k has additional tax benefits over an IRA when investing into real estate using leverage.

not hard money just traditional lenders, but not sure how to search.

I'm playing the long game and not looking or needing to cash out any properties right now. 

Hello all, I have been investing in both a ROTH SDIRA and a Traditional SOLO401K plan for a few years now and have things going pretty smoothly.

We do know we want to go the traditional route.

The roof condition will make it difficult to get a traditional mortgage, whereas I have talked with some local credit unions who do a “desktop underwriting” value of the house when they run the numbers for a HELOC.  

Most of this is a numbers game and the boss has you doing the grunt work, maybe bring it up to him and see if he has experimented in the past with timing or if he hasn't suggest it now.

It takes  much more work and time than finding a "good deal" that qualifies for traditional funding from other lenders.