Fast forward to the tail-end of my second deployment and I'm finally debt free, saving up enough to have rehab funds to accompany my VA loan for the first property.Where did you encounter the most friction when you started off?

Also looked at STR comps for daily rates to see what is more profitable but can't seem to make head nor tail of it unfortunately.If I were to take a guess I would say studio's & 1/1 are probably are more profitable for us owners and multiple bedrooms being more profitable for the STrenter!?!

Not a big deal if you're at the tail end of the agreement, but could be a lot if you're towards the beginning.If there's anything we can do to help please feel free to reach out, PM recommendations or advice.

Tails and it’s a bad deal

Until you become laser focused, your like a cat chasing it's tail and will never get started.Real estate development is huge risk, you can have huge rewards but you can also get go BK in mins.

I am at the tail end of 35 years at this and selling off all my rentals the last 3 years so been dealing with the recapture.. 

This is not just a question of looking at comparable sold homes, it includes evaluating current pending and active homes  so you can catch trends as they are happening, and also understanding seasonal market trends so that you don't price on the higher side in June/July when you may be at the tail end of a rising spring market, or under-price in February because you're looking at comps that sold in December and January, etc.And it includes understanding the home features that are going to add or detract value compared to the comps, i.e. great house but unusually small master bedroom/or backs to busy street/or missing that one extra rec room or flex space that will keep 3 or 4 people from piling up on each other. 

Believe me, I am taking notes as we now reach the tail end of the disposition process.

So could I move forward with a 1031 exchange + primary residence tax benefits if for the full 5 years, the second floor is rented out and I only live in the first floor unit for 3 years, then lease it to tenants for the other 2 tail-end years?

Don't let the tax tail wag the dog it's attached to.Just plug the state taxes into your numbers.If the numbers still work, then go ahead and invest in the state that has taxes.If the numbers don't work, then don't invest in that particular deal and look for others.