To be safe, go ahead and sign a buyers rep agreement (even if for a short time to cover the duration of the negotiations) That way you know for sure it is not a Sub-Agency.

What are your thoughts on purchasing a multi-family property, live in it during the duration of school and renting out the other halves?

The toughness seems to be defined by FCL duration.

Also, the tenant seemed to have a significant interest in buying the property too so that may indicate a longer duration to live in the house.As for costs, calculations, and cash flow, here's my math:Income - Expenses = Cash Flow/Month.Income(Rent) - Expenses[Property Tax + Insurance + PM + Mort. + HOA + Vacancies(10% rent) + Repairs(5% rent)] = CF/M.Income(2500) - Expenses(PITI + PM + HOA + Vacancies + Repairs) = CF/M.Income(2500) - Expenses(1670 + 0+ 0 + 250 + 125) = CF/M.

Could be a win for him on the tax front and a win for you if you could negotiate it close to 5% and keep it that way for a large number of years or perhaps the duration of the loan.

(will need to find new tenants for both units soon)Contracting all repairsPros - Shorter duration, lower holding costs, more time dedicated to tenant screening and property management, begin developing relationships with contractorsCons - Higher labor cost, harder to develop specifications/standards, less money available for future investing.What are other folks doing out there starting out?

If I buy at low rent to price ratios it is usually in good areas with good mechanicals that I expect will allow me to be under the 50% rule for the duration of my 15 year financing.

The duration for which you hold a rental before selling is what determines the tax rate IIRC.  

How long is the duration and how sensitive is it to market cycles?

Especially being a female investor visiting vacant houses all over duration.