@Jason BocekIf you plan to file your own return - You should look into reading the following form instructionsSchedule E - supplemental income and lossesForm 4562 - Depreciation & AmortizationForm 8582 - Passive Activity Loss LimitationsHowever, you may be better off find a professional who can prepare your returns correctly and provide you tax advice.Your rehab expenses may need to be capitalized if it was paid before the property was livable.You should be entitled to other expenses outside of interest, taxes, insurance(remember paying down loan balance is not a deduction).You should interview a couple accountants here on BP.

I know it's not ideal to start in this situation but in all honesty to some extent everyone in this industry does it. 

I want to get my hands dirty on this first one.... and ideally double-up every 18-24 months.

One thing to remember about inspections is that you are paying someone to look at the property and find all the problems.  

I don’t remember the addresses, but one was a 100 year old duplex with major structural issues surrounding a central stairwell and the other was a 1950’s build with a block wall tuck under garage that was beginning to shift, causing issues throughout the house.

Of course ideally you get both in one property but that's tough to do unless its an off market deal or you predict the right area and get in early.

Remember, an appraisal is just one person’s opinion of value.

2) When looking at cash flow, remember the coveted "1% rule" here on BP- where a GREAT cash flowing property will rent for 1% of the value of the home each month.

Ideally I’d like to keep one of the units but move proceeds from the other two to other long term investment property where it doesn’t snow. 

Also remember sometimes it's better to take a higher rate if it means lower cost to close.