At the same time I guess those HOA fees could just be put into a future repair fund for single family homes.

You have to make sure the person or company over the association is not siphoning money and is also being a good steward of the funds balancing the budget and tracking repair items.Special assessments could kill your cash flow model.

It will be reported as rental income.You will also be entitled to take ordinary and necessary deductions used to upkeep the rental business which includes items like repairs, utilities, mortgage interest, real estate taxes, depreciation etc.

I have a security deposit to cover this but wanted to check to see if anyone knows an efficient and fair contractor to hire for a crank window repair services.

4 - If the answer to #3 is yes, during that 20 year period, what extra costs are added to the total based on repairs, etc...that also must be caught up before you break eve...and start to actually make money?

Make sure that if you do find a property that it will cashflow with vacancy rates, maintance repairs, and potentail management fees included. 

There should be a budget for repairs.

Some are nice and need little work and some are beat to death and would need major repair work. 

Do you need to finance the repairs or can you pay out of pocket.

Plus, the condition should match, if the house is going to require significant repairs it's probably more efficient to save for those and pay them off vs dump it all into the note.