All of these sellers want to sell and we had good conversations but only a couple have flip opportunities...just not enough meat on the bones.

The positive outlooks, the honest reflections, and the bare bones message of "Just believe in yourself and give it a shot!"

We are very interested in a Buy and Hold strategy.I do have some basic construction skills, so I can spot things in homes we are looking to purchase and estimate how much it might cost to repair.  

To do so requires an intimate knowledge of the areas, streets, tenants, city, rental laws, and everything having to do woth construction

There is essentially no difference in the two plans you laid out.Plan A:  Each of you files two Schedule Cs for half of everything orPlan B: One of you claims all of the income and expenses and then "hires" the other as a subcontractor.  

Plus we were the first tenants in his new construction.

(people pay a lot for that though)i currently work in construction and my girlfriend of 5 years is working on her RE license right now i have definitely been reading her books as she finishes. following her into that sounds like a good idea. i had also considered getting into home inspections.

I'd love to pick your brain about what the status of the wholesaling market is here.I have a background in construction and construction project management so I expect fix and flipping to be in my future once I get the ball rolling on the cash side.Osiris

I don't make much money but I cut my living expenses to the absolute bone to save for houses. 

Your job as a wholesaler is to find deals you can pass on to other investors so there needs to be meat on the bone.