We would like to do it all legally with plans approved by the town.Any recommendations for an architect / company that can assist us with this project? 

If not, I would recommend purchasing as it is worth it compared to a large investment you are about to make...

Which syndication software is recommended to keep everything streamlined?

If you're looking for higher cash flowing markets, I recommend starting in Midwest because it's affordable and offers good cash flow.

Your strategy is possible but I would still recommend speaking with a CPA to ensure you understand depreciation recapture and intricacies of a 1031

If I was your brother getting my REI portfolio started, is there any advice, strategies, links, literature, articles, or people to follow that you would recommend for someone extremely leery of financial risk?

Beth, I strongly recommend Aleka DeGraaf from Acorn-Oak.

Can you recommend a good one? 

We try to do a walk-through with the new tenant at some point to show them emergency shut off locations, instructions on filter changes, etc. so I wouldn't recommend just dropping keys off and that's it, but I have had probably 2 or 3 tenants over the years that I never met, just talked to by e-mail or text.  

Hi, my name is Jacob My question is:As a beginner to Direct mail, what would you recommend for me when first starting out, What pitfalls should I avoid that most beginners endure, and how should I design my message to the prospect to get the most consistent responses?