I live in san diego ca and plan to move to chicago to buy a triplex and make brrrr in the future.

I also plan on developing an ADU to permit 2 + beds 1 bath unit and community improvements such as installing solar panels, specified parking areas, common areas, a community garden (for tenants only), and rehabbing each unit to force appreciation.  

Prior to this I’ve lived here around 6 years and always paid my rent on time faithfully and plan on setting up auto-pay to avoid any discrepancies in the future but I honestly can’t afford to just give away an extra $370 if I don’t owe it.Any insight into the discrepancy would be greatly appreciated.  

I do plan on getting one more home in MI to be a rental (1 primary and 1 rental in MI LLC), I will use them the same way i did this AZ home.

Target a price based on where I am in my REI plan, which has a specific amount of cash available, and a specific return needed from that cash, at the specific timeline in my plan. 

Good luck, I will be happy to hear from you if you proceed with your plans!  

Unfortunately the company I am leasing through does not allow extensions as that was actually my initial plan!

https://mioym.com/Who are you planning to sell your fix & flips to in the Detroit area - investors or owner-occupants?

Living in your home the next 2 years to avoid capital gains tax only applies if you are planning to sell it within the next 5.

Once you can answer all these, and develop a long-term plan, pick a market that accommodates your goals as well as your budget and criteria.