As others have recommended, I would suggest looking at starting with buying a primary home with your VA loan - whether that be a single family home or a multi family. 

Thanks for the suggestions!

Hi Tyler, A blanket loan may be the best solution for you based on the price points of the properties you are targeting like @jacob Sherman suggested. 

Wonderful taxpayer funded heat map block by block.....  

Now the minimum standards your basement has to hit for it to be able to count as assessed sqft not estimated is a height of 7 ft, a point of egress (bilco doors) and a window usually in the rear, It's one of those things where if your going to go through the process of digging out a basement you might as well go for it and dig it deeper then 7 and closer to 8 ft so you actually stand out compared to the competition.Now the other side of this coin which I would suggest is if you're willing to spend 40-50k on a basement dig, consider adding a 3rd story addition if your a 2 story (think master suite, walk in closet, master bath) or an addition off the back and add a roof deck if your a 3 story (either master suite or just additional bedroom).

I suggest to look for local meetups in your area, these can be a great way to meet other investors, share experiences, and learn from each other.

I am wondering if anyone out there is a financial planner and/or CFP and has any insight on the situation as I think about it.

However, I would suggest double checking the rental income.

Do you have any suggestions with how you would tackle the pitching?

Does anyone have any suggestions on where to find a template like this that can be electronically signed?