Since you own multiple properties we have a market which will write you a master policy and schedule out your properties on one master policy to save you money and paperwork.

If you’re working with a tax professional ask them to do a tax projection for you with one scenario assuming you sell all 5 today and the other assuming you only sold 2 today.With the tax projection you’ll now have a good estimate of what your tax situation will look like and can make decision based on that.Maybe you can consider selling your portfolio and doing an installment sale, this won’t help on the depreciation recapture but it would help spread the gain over multiple years.Each strategy has pros and cons, if you want to rip the bandaid off an be done cold turkey (or warm turkey if you’re into that) there most likely will be a large tax hit but less headache holding them longer.

I’m thinking one possibly multiple sub 1000 sq ft cabins. 

I had multiple offers, and a couple from Chile purchased it to move in for a couple years and convert to an Airbnb.

I have been looking at CRM's like Hubspot and Odoo and I tend to get a little overwhelmed because their tutorials all seemed to be geared towards those that have multiple people working on the CRM and all of this automation when all I want is a simple database.

There have been multiple delays and price escalations from the home builder and very poor communication.

Go to Etsy and search for "rental property tracker," and you will find hundreds of nice spreadsheets to track 10-20 rentals, usually for under $10.Software has extremely helpful features like online payments, marketing syndication (click a button, and your property is advertised on multiple sites), electronic document review/signing, maintenance tracking, and owner reports.

Some HOA's may cover 1 or multiple of these 4. 

These will be done in multiple phases. 

Lastly a Heloc will "Never" act as an asset or PITI reserve so if you fail to have sufficient funds required in reserves (Cash) then your will not buy multiple investment rentals.