After 12 years I am winding down my business and relocating from Los Angeles to Massachusetts, for a life overhaul. I have an owner/user office building that is going on the market now. I have always had 1 and sometimes 2 tenants (besides my operation) in my building depending on the expansion and contraction of my operation. The time it takes to sell the building will dictate when I close up my business. My wife has already relocated and is working and living (renting) in the area that we are moving to. Our long time LA house is on the market and will likely close in the next month or so on that. That cash will earmark to purchase a home next year.

I will 1031 exchange the building. My instinct and genuine personal interest is to move in the direction of the multi-family business. I expect my net proceeds to be between 800k and 1+million depending on sale price of my space in LA. I have learned that I will have to exchange with the LLC that I own the building in which is a California LLC. It is unlikely that I will buy apartments in the area I am moving to as I desire higher cash flow than might be available, so i can live off that while otherwise I re-invent myself. And so I expect to have to look markets other than California or Massachusetts. With a good property management company, I am quite comfortable not being across the street from it. With the amount I have to work with I could potentially end up with 2 buildings with many units in them.

The main point of my ramble is I want to be talking ahead of times to lenders, and I do desire to leverage out my proceeds to the point that is reasonable and profitable and with 25 percent down that could be 3.6 to 4 million in purchases. However I am not clear if my track record as a business owner and of a commercial building is the kind of experience that is expected of someone trying to leverage out to bigger multi-family buildings. I otherwise have good credit and other assets beyond the building and the house and multiple years of profitability in running my business. Do I just start talking to lenders in one of the potential areas? Or is there a more generic "rule of thumb" without spinning someone's wheels too much? Which cart goes before which horse?