HUD would consider an office or living room as a bedroom for occupancy purposes per the Keating Memo.

Definitely consider an LLC now, it will improve credibility on your first deal in presenting an LOI or even approaching a broker/vendors, lenders, etc.

You may want to consider an LLC for liability purposes.A road association can be a big selling point if competing properties don't have one - especially if the roads are dirt. 

Consider an "open house" showing and tell everyone they can show up on Friday, 11am - 1pm to view the rental.

If you're looking at residential mulfi families (2-4 units) you'd likely get some type of 30 year fixed product and your lender would be able to give you a pretty good idea on the first call/meeting what your interest rate would be (after pulling credit), type of loan, downpayment, as well as closing costs for the loan.If you're looking to make offers on properties in Boston or Massachusetts area, sellers won't even consider an offer without a preapproval/proof of funds.

If anything you may consider an appraisal gap instead of waiving financing contingency.

Yes, if you further get rentals, later on, when you have over five or six, you can consider an LLC.

Consider an FHA loan if you go the route of a multi-unit property, as you only have to put 3.5% down. 

Buy the Max. allowed on the policy ($500,000 or $1,000,000 normally) and consider an Umbrella policy for more coverage. 

On my 2nd career loan, I had to get past this condition because the subject property was more than 100 miles from the employer, which most would consider an unreasonable commute.