@Shaylynn O'Learyi understand the frustration of living in a high cost market and looking at the appealing price points in those other markets. 

It would be smart to do a full lease audit, estoppels issued, and tenant interviews.And if you are buying cash, there is nothing mandatory, since it is your money at risk. but again, physical condition inspections, understanding of tenants (they are a great source of information about issues with the property that the landlord may not know or may not disclose), surveys to understand accurate property lines, etc.

Some quick googling suggests the answer is yes provided I don't rent it out more than 180 days for the first year, do I understand correctly?

Many S8 tenants are getting free rent money, yet don't take the time to understand the program and dump everything on their caseworkers and landlords!

Depending on these answers one lender who charges 3 points could theoretically have lower total transactional costs than a lender who charges only 2 points and its important to understand all fees associated with each lenders origination process. 

I would recommend house-hacking or partnering/mentoring to get a better understanding of real estate on your first deal. 

Hey Chris, a few thoughts here.Considering that office is not attached to the house, I wouldn’t add any footage to the total home square footage; however, you could advertise that office space and amount of footage and amenities in your remarks.If you’re a Realtor or are using one for the sale, your local MLS may have fields dedicated to additional footage for other buildings on the property, such as ADU’s.The other point is that typically, perhaps depending upon location, a space needs to have heating to count in the square footage, which this office doesn’t have if I understand correctly.Consider contacting an appraiser to inquire about how they would handle this space on an appraisal, or a Realtor.

Thanks ChrisIt would great if you could help me understand the type of data analysis needed and if you need such service which I can be of help.

A good lender should understand that.

I typically look at Zillow, centimeter and BP to get a full understanding of what rents are in the area to get the best estimate of what a property would rent for.