That said, let's talk about the alleged sticking points: a heated drive in a colder climate is DEFINITELY attractive (...says my aging but stubborn snow-shoveling body in New England.)

Canadian, Wisconsin and Minnesota snow birds winter here.

I need to sell all this Chicago stuff that gets snowed on and go buy a 200 unit value add in Phoenix :)

JeffListing Price:$159,000 INCOMERental Income$1,748 $.85/sqft.Garage$0 Laundry$0 Storage$0 Misc$0 Total Monthly Income$1,748 EXPENSESTaxes, Property$350 Insurance$100 UtilitiesElectric$0 Water$100 Sewer$50 Gas$0 Garbage$0 HOA$0 Lawn/Snow$0 Vacancy$100 Repairs$100 "Capital Expenditures (i.e. new roof)"$150 Property Mgr $0 Mortgage $705 Total Monthly Expenses $1,655 CASH FLOWIncome $1,748 Expenses ($1,655)Total Monthly Cashflow $93 CASH-ON-CASH ROIDown Payment $15,900 10%Closing Costs $5,000 Rehab Budget$5,000 Misc, Other  $0 Total Investment $25,900 Annual Cashflow $1,111 Cash to Start: $25,900 Cash-on-Cash ROI 4.29%

Probably something simple I am missing or the deal just doesn't make sense.3 condos, the owner has 14 out possible 48 in this complex and if the deal goes through may lead to more deals with her.the condos are 1/1, 2/1 and 2/2, she is asking 76k for the 2 2/1s and 64k for the one bedroom. total 216k, she would hold a second position note for 30k with me putting down the remainder of the 20% down (13,200) and pay closing costs. she would like 6 payments, one each year of 5200 for 6 years which comes out to 31200 total, about 1.5% interest rate if my calculations are correct.For simplicity, I am counting the 3 as a triplex, so rental income is 2325/month, tenants pay for electric and gas, HOA of 185(555) per pays for water, sewer and garbage as well as exterior and common area maintenance, snow removal, grass cutting, etc. taxes are 266 and insurance is 50 month (HO-6) policy which I hadn't heard of before.

I've had a few discussions about the best way to create a plan in order to "snow ball" your way to owning many REI properties (buy and hold for rent).After Googling around and even reading blogs on this site, I've thought about doing something like the following:Buy my first rental property (SFH) with cash (around $60-70k) where I'd expect about $500 cashflow per monthCurrently I have about $105-110k available (after taking out an emergency fund)Then shortly after, buy my second rental property (SFH) but take out a mortgage and put down around 25% on a $60-70k houseThe cash flow on this property specifically would likely break even (at or near 0) but this would be on a 15 year mortgage and I can use some (or most) of the cash flow from the first to help pay down that mortgage faster, along with my corporate job monthly savings tooI feel I could pay it off anywhere from 5 - 10 years depending on the exact strategy If/When I get the 2nd one, then shortly after that, try and get a 3rd SFH rental property and continue this snow ball effect to build up by rental portfolioObviously this is easier said than done, along with risks and I honestly do not have any real experience with rental properties as this is my first time diving into this type of investing.My main questions would be -- Has anyone done a similar strategy to help build their portfolio quicker?

In my lease I have them pay all utilities, do their own maintenance (i.e. snow removal, lawn care, etc.), and tell them to take care of the property as if it were theirs.

You can put one staircase up the middle which would make sense if you were in snow country but you are not. 

I think some of the siding may have also been damaged by snow or ice sliding down the others roof and probably into the side of my building.

When you have temperatures below 0 and a couple feet of snow, people are much less motivated to move into or around the area.