I hope your not purchasing these at high LTV and expecting positive cash flow.  

Focus on your current sales position and continue building on that.

:Class A Properties:Cashflow vs Appreciation: Typically, 3-5 years for positive cashflow, but you get highest relative rent & value appreciation.Vacancy Est: Historically 10%, 5% the more recent norm.Tenant Pool: Majority will have FICO scores of 680+ (roughly 5% probability of default), zero evictions in last 7 years.Class B Properties:Cashflow vs Appreciation: Typically, decent amount of relative rent & value appreciation.Vacancy Est: Historically 10%, 5% should be applied only if proper research done to support.Tenant Pool: Majority will have FICO scores of 620-680 (around 10% probability of default), some blemishes, but should have no evictions in last 5 yearsClass C Properties:Cashflow vs Appreciation: Typically, high cashflow and at the lower end of relative rent & value appreciation.

Trouble starts when owners “live off” the entity, instead of taking a salary or owner draw.  

Even if you decided to do MTR or STR, you would be hustling just to be net positive.

- How can I best estimate a breakeven point, and what techniques help maintain positive cash flow through all stages?

Use a 1031 exchange to defer taxes and reinvest in more lucrative, cash flow-positive properties or diversify into passive investments like syndications.Pay Down Debt: With limited cash flow, focus on paying off the HELOC or smaller mortgages.

@Sarah Rhee - Sorry to hear about your troubles, but it sounds like you are in a good position networth and equity wise.

Yes, the sentiment toward wholesaling is not very positive--especially in an oversaturated wholesale market like Orlando.  

Less sexy coc returns but cashflow positive day 1.