This tactic is good because you are building a reputation with that agent to be consistent and reliable till they give you a yes, and that agent does not have the capacity yet with a big team to manage the listings and open houses. 

With a turn key provider, I would say that you can get some good property and that is definitely an option, but it can be difficult to decide who to use and who is reputable and then to actually look after your portfolio once it is purchased, may be a different story especially if this is a long way away from your home base.  

This scenario isn't what a VA loan is for, so you have to explore other options.Stephanie 

.), keep working at deal analysis so by the time I'm ready to buy I can run my numbers, and finally explore other options to investing in Chicago.

It's what I am trying to discern for the market I am exploring now (on the Treasure Coast because it is driveable for me- can't afford a shack in Palm Beach either :-)). 

.- All assets are removed from your name which will normalize your FICO credit score-They will require quarterly updates on your books-5-10 year balloon is the norm but expect prepayment penalties- Lender holds 3 months of reserves Here was my breakdown when first exploring this: https://www.biggerpockets.com/...Properties 20+: PLAY WITH THE BIG BOYS:Flush with cash after the cash refinance and hopefully additional capital the number one priority is acquiring properties.

I have explored multiple creative financing strategies on this one and none have worked for both of us yet.

Just exploring options.

You may want to consider exploring the possibility of working on a larger team, rather than on your own, as they might have the support staff and other team members that can work with you and your clients in order to still provide the same full time/full-service experience customers expect.

In order to be successful at it, I would advise developing your Core Four: investor friendly realtor, reliable contractor, sophisticated lender and a reputable property manager.