It is a TON of work but you only need 1 to 2 deals per year to live the good life.

I’m trying to familiarize myself with the area more thoroughly.it seems to have a stable increase in prices.Since I plan to live in the property initially, breaking even in the first year is my main goal. (5% down; PMI removed with renovation)However, I’m also wondering if it’s feasible to have some cash flow from such rentals, or if the risk of vacancy is high in this market.Any guidance or pointers from those experienced in this area would be greatly appreciated!

I also never lived east of 33rd Ave at that time. 

Additionally if you are deeding the property you live in to an LLC you may lose the homestead exemption which could actually increase your taxes. 

I truly appreciate you sharing these takeaways—it’s clear you’ve not only thought this through but lived it.I took some time to explore your Linktree, Instagram, and the Elevate CIG website—truly impressive work!

Hey Jack,I'm currently living in R.I and I grew up in MA.

I guess I could do some work-arounds -- maybe reserve one unit in the first purchase for use as an AirBnb, and reserve my own time in it when needed - instead of claiming it as a primary.Are either of you (or anyone) familiar with a finance product/loan that will allow me to purchase under $150,000 (w/ strong credit) and do much of my own work and live-in a portion as a primary residence?  

This family member does not live in the condo and it's valued upwards of 1M.

I am looked at by the loan officer as living in a situation rent free. 3.

I never actually went live on the site because of the 15% fee they wanted.