A few takeaways for us:-we were able to rent back because we had an alternate short-term living situation lined up with my in-laws (free rent)-we had to limit the rent back to 60 days max because of our mortgage terms (required owner occupancy within 60 days)-we didn't use a long lease or anything.

Before you purchase a property, I would suggest going to your bank and applying for an increase in your credit card and line of credit limits (don't use them, just have more space available).

It seems to me that there's a hard limit on how far they can rise without tanking the entire economy given the level of public and private debt as well as the impact on financial markets. 

That said, size rather then specic rooms usually controls the sales price. 

The limitations on those loans is not that you can have up to 10 conventional loans. 

I'd give it a try since your time is limited with getting a tenant in before vacation.

Parking in NYC is limited.

You will have an entitlement limit of let's say $450k, you could in theory buy two homes in different areas if your total loans between 2 homes are under that $450k.

That seems steep, I pay $550 for the same type of SFR with Allstate but you may have different limits than I

Most bid jobs have a time limit which is usually 30 days.