We have already talked with multiple HVAC contractors and splitting to two zones is just not an option because of steam heat.

No but you could create an excel macro to do multiple properties at once - also the numbers that someone provides to me I take with a grain of salt anyways. 

Most people cant afford that alone which means a syndicate or getting PMLs involved and doing the synd yourself. there's nothing wrong with starting with some smaller properties.

The multiple offers come, but not all the time these days 

Mostly due to the fact my spouse and I agreed on her to have zero involvment in any sort of RE investing (and its our home) I think once you have a good 6-12 months of reserve cash (operating expenses for your own life saved as a back up incase things go bad) save enough liquidity to get the ball rolling on your first invesment.

Whether it's considered an arm's length transaction is debatable, but it's not illegal.Move forward with the sale and ensure full transparency with all involved parties, including your CPA.

Let’s break this down:The Pros and Cons of SellingPros:Unlock Significant Equity: Selling would give you $500K in cash (less transaction costs), which you could reinvest in multiple properties in higher cash-flow markets.

Quote from @Tod DuBois: Hostaway appears to integrate with the multiple channels - but I hate to do a software setup and learn it's not a good place to do what I need to get done (which is work as little as possible and optimize my occupancy).

Sales team is dishonest, multiple people get stolen from by members in the community every single week.

You could also consider a reverse 1031 exchange, where you buy the new property first.Make sure to identify multiple properties (up to three) to keep your options open, and try to negotiate longer contingencies with sellers.