I never consulted with a lender, realtor, experienced investor... no one!

I mentioned the idea to my previous lender and he was saying about the same $100K-$150K.  

If you are financing the purchase, the lender will also provide protection, you will get an inspection done to protect you and so on.

Have been working with a lender the last few months.

I think when one is starting out, you want to go lower than competition, but not so low that you attract the wrong crowd, so that you can build momentum and reviews.  

I've got an agent who sends me deals, some of which are off-market, contractors who can do the work, a hard-money lender who seems to offer good terms, and a property management team I trust.

If I understand your situation correctly, you could structure a Tenancy In Common (TIC) deal where each of the separate LLCs owns an undivided interest in the replacement property, as tenants in common.These deals need to be structured properly and you need to have an attorney familiar with 1031 exchanges involved to make sure it's done properly.Also, if there is a lender involved, that can complicate the matter as well.It's definitely doable, if you have the right professional help while you're doing it.Feel free to write if you have any questions about this.

To be honest, on over 100 building permits last year in the City of Chicago, with many of them having some form of enclosed porch, I think only 2 were ever mentioned by the Department of Zoning where they brought it up as a "Concern" which led us on a wild goose chase of finding and sharing information, overally causing unnecessary delay to the permit review process and eventually coming to a close (some positive, some negative).

There are lenders who will do vacant land.

Because you’re getting within 12 months of leaving the military, many lenders may want to see info on your next job for income.In addition to the VA loan, check out the NACA program at NACA.com.There are many lenders.