We (I work at Azibo, just a disclaimer) have quite robust accounting capabilities and time saving features like Schedule E generation and automated  transaction tagging rules.

I do like many things about Bolt - they have great customer service, you can schedule calls with a business planner/teacher, etc.Hopefully this was helpful!

I rented it weekly for about seven weeks this summer and I have a handful of future rentals scheduled for September and October.

the market is unforgiving right now and no one is going to look out for you the way you will look out for you.Yes, I'm planning to schedule some time to visit the market.

Discuss the terms, including interest rate, repayment schedule, and collateral.

This is very similar to my schedule (some of the bulleted content you have may vary or be included with other messages) but since I've also starting using Airbnb recently as a guest ( a lot ) it is interesting to see what hosts do and this does feel like a lot (hence the contradiction).  

Pros to my current position: Secure, w2, pay is above average, benefits are stellar, schedule is somewhat flexible (can leave if I need to without penalty; vacation when I want - utilizing banked time on both), 3 miles from home, and hopefully a pension in 17 years. 

We do work crazy hours sometimes but my schedule is mine and there is no limit to the income I want to pursue.

It's a suite of applications that includes all the same things Google docs and email does, but also has other programs like a CRM, scheduling (like acuity), meetings (like Zoom), dropbox-like storage, Flow (like Zapier), and invoicing.

Both you and your wife should take the time to schedule a session together with an asset protection attorney who knows Connecticut and New York law.Good Luck!