What I'm having problems with is thinking of all the items to take into consideration when calculating operating expense ie property taxes, repairs etc.

Would consider CAPEX those big ticket items you would see every 5-10 years..ie New furnance , new roof, HVAC ro water heater.

Lastly, if you rehabbing yourself to keep or flip vs wholesaling, I would have about 10-15% contingency in your estimate for the unknown items that pop up during rehab.

That assumes you have something in the lease that says such items are "due as additional rent".

If you are not totally sure how much certain items might cost you IN YOUR city …would you recommend insurance adjuster tool called Xactware ?

I realize that all items for the rehab work clearly need to come from the SD401k and that I would not be paid for any time and expenses for such an endeavor.

They can help you set up your depreciation schedules and guide you in how to correctly itemize your expenses.

Next I'd find out how much I'd need to pay for the following items: Taxes Sewer and Water Trash Heat/Utilities HOA Cap Ex and Ops (how much are you going to save each month for everything from changing community light bulbs to replacing roofs) Insurance Mgmt Fee (as a %) Vacancy (as a %) If all of the above plus your mortgage payment (principle and interest) left me with $100/door/month profit AND 15% ROI (cash on cash) I'd start the negotiation process.

You can also set key word alerts for items or areas of interest, like "North Carolina"

Unless your A. a contractor or B. someone whoes previously replaced all the items the HOA controls, who really knows how much the HOA is going to cost you in the long run when they dictate such things.