I don't know the cost of things in your area but you would get the proceeds of the sale tax free from federal income tax from the primary residence exclusion.

Much of your “income” will come from appreciation, cash flow won’t make you free.

Fell free to message me with any questions!

If you can't and have to hire a PM, I recommend you get some kind of "guarantee" from them that they will replace the tenant for free under certain conditions.

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.

If you have any other questions, feel free to DM me! 

No one works for free

Cost segregation companies offer free cost/benefit analysis quotes to help you decide how beneficial the study will be for you.

If you have any MA questions, always feel free to reach out.

Feel free to reach out if you have any questions or need guidance on your journey.Again, welcome to the community!