Should I Buy or Hold? Seems complex!

[Kevin Z.]

I consider myself a numbers guy, but I'm not sure what numbers to use to help me decide whether to buy or sell. I'll try to be as specific as possible. I'll answer any questions if it helps you...to help me!

I own a SFR and a 3-family. I am very limited with capital right now due to a long rehab project on my 3-family. I only have a couple of months of reserves for each property. Here are the basics of each:

SFR

Value-$325K. Rent covers mortgage +$400 each month. Awesome tenants who take stellar care of the property. It was my home until 2 years ago. I am hearing the clock ticking on my chance to pay no tax if I sell. I could make about $80K-$90K if I sold. Mortgage is 2 years into a 30-year mortgage and pays down about $365/month. I could get about $25K-$30K out if I chose to get a HELOC.

3-Family

Value $700K. Currently empty. Should rent for mortgage + $1700/month. Could convert to condos and make about $100K. Mortgage is 2 years into a 30-year mortgage and pays off $480/month. 

My Goals

My goal is to BRRRR and enjoy a little cash flow with the advantage of not having to save a ton of capital (I'm *only* a teacher by day). I live in Massachusetts where things are pricey (multi is in MA, SFR is in NH). I want to get over my fear and look in different markets and no longer self-manage.

My question, other than, "what would you do?" is one of how to do the math. I feel in some ways as though I have a bit of what I want, namely some cash flow, so selling feels a bit like it would defeat the purpose. On the other hand I don't have the capital I need to grow. 

If I look at the $765/month that I make on the SFR between $400 cash flow and $365 mortgage pay down and divide that into the $80K I could make from selling, that shows me that it would take 8.5 years for the renting to equal the amount I could get from selling. Not to mention the taxes on a $325K sale that will not be forgiven if I wait more than 1 more year.

If I were to sell the 3-family as condos and keep $100K, or $75K after taxes, that would equal almost 3 years of rental income plus mortgage paydown on the multi. 

I realize that I am excluding tax advantages like depreciation, but my head is ready to explode as it is!

I'm feeling inclined to sell the SFR and keep the multi. But maybe there's a better way to analyze the numbers that I'm not getting. So, would you sell one or both to gain capital, or would you save up the cash before looking to invest in a cheaper market?

THANK YOU!

Kevin