My favorite is using the Intuit Self Employed App because it automatically tracks miles as part of the monthly price and updates your expense tracking.  

I wish AirBNB was as user friendly as VRBO.I don't go into AirBNB as often because it isn't as intuitive and maybe thats one reason why I'm not as comfortable using it since I get frustrated when I try and find items that are buried.I get most of my bookings and I get higher per night prices on VRBO.

The reason I say fast here is because you want to be using your gut/intuition on your initial decisions.• Now, spend 1-3 hours and call every single one of the accountants.

Personally, I find #3 to be the most valuable as it lets me know if my spreadsheet + intuition ultimately matches up with the sale price.  

They're both great imho.Hoboken will be fine in the long run, but your intuition about a soft patch is most likely true.  

I can't guarantee you squat as I'm not your lender, but this is what the guidelines say...On top of that, your occupancy intent needs to make intuitive sense. 

I know it sounds counter intuitive, but you can increase your passive income by claiming everything legally possible as capital expenses. 

It may sound counter intuitive but if you can find an investor locally who is willing to let you split the cost of investing and split the cost of the profits you are far better off.

Thanks for your opinion on when is 'too far', that aligns with my intuition.

You do this long enough however you do not need some checklist in front of you, and it becomes more about intuition and experience that you are pulling from to know what a good deal is and what is a deal to let the hotshot fly by night person try and make the buck with.