I have bought 2 properties this calendar year and this feels like the right next step to further me along. 

I have a feeling things will work out a lot better.

Hopefully after our conversation, you have a better feel for what to expect.  

Depending on your area, it can be a pain to set up multiple LLCs and keep them running.

A 1031 exchange is NOT available for owner occupied property so that’s the bad news.The good news is for owner occupied primary residences, for married couples, the first $500,000 of pain is tax free.No need to worry about a 1031, live in the house, sell it, use the $500,000 exclusion and you pay KP tax on whatever profit may exist,2.

Prices go down, causing financial pain for the gentry.

It took a year of painful lessons (the first of which is that NOBODY will care about your business as much as you do (Evolve), and that - in my case at least- self managing makes more sense -even remotely- than allowing someone else who has different motivations to take the reigns. 

If you can't tell it's a royal pain!

Then you need to add in pain in the *** factor, which for an older expensive property while you live abroad is quite high.

Which is to say any attempts beyond the method of communication in the profile are likely to end up convincing the landlord you and your friend would be a pain in the butt as tenants.