this is where the gray area comes in with accounting.

@Zach Howard I am working on a how-to book on Creative Financing now (I am the author of BP's book on Mid Term Rentals) because when I was teaching myself I was frustrated at the lack of clear instruction.

Had a quick question.I purchased the property for $500K about 10 years agoI'm selling the property for $575K with the Fire DamageI received an insurance check of $380K for the fire damage.After Paying off the Mortgage + Escrow + Realtor Fee's, I'll be left with about $150K.My question is will I get taxed on this $150K?

I am not a PM, but I do self manage about 50 units.

I would do the deal if I were in your shoes.

If you do not, I would still love to connect sometime when time permits.

At least starting out.

I would suggest you do both of what you suggest - meaning get either a new mortgage (more conservative route) or HELOC on the townhome and use those funds to buy your next investment property.

Depending on where exactly the property is located they may have some different rules/laws in place.

I personally have no connections with anyone who is involved in this niche and I'm wondering how other people have started their journey.