Look for a distressed property that doesn't need a major rehab but does not some cosmetic work (paint, floor, cabinets refinished, landscaping, etc).

You also didn't mention pest control, landscaping / lawn mowing / lawn care, booking fees, resort taxes / hotel tax that you'll have to pay, supplies, and possibly property mgmt fees (depending if you self-manage).- Finally, since most of the income comes in during the summer season, you must be prepared not to use the place during the summer season (which of course is the best time!).

@Robert Jones Chicago has a diverse investing landscape so it's difficult to answer this question.

I was instructed to build a team that consists of:GC, plumber, electrician, HVAC, landscaper, floor installer, roofer.It was my understanding that the GC should do everything that is not covered by one of the others. 

Significant unit interior remodels (19 out of 24 units) and minor exteriors/landscape updates.

Which means your home, especially landscape maintenance, can lack the attention needed. 

Same goes for 15-year property ('land improvements, i.e. landscaping, pavement, fencing)Bonus depreciation allows you to either claim 50% or 100% of the depreciation of those assets in the FIRST year!

I have noticed the Real Estate Landscape has drastically changed over the years.

Later we spent money on landscaping the property professionally, which has been one of the best moves.

.- Purchase price: $87,000-Rehab Cost: $30,000-Total Cost: $117,000- Loan payment: $491.83 (principal and interest only) With financing at a 3.5% rate - Property tax: $520.83 (Too Damn High For The Area In My Opinion But I Digress)- Insurance: about $200 per month - Management fee: $220  (10% or gross monthly rent)- Maintenance/repairs (reoccurring): $220 (estimated 10% of gross monthly rent) - Vacancy: $110 per month (5% per unit per month)- Landscaping: $100 per month- Total monthly expenses: $1862.66- Rental Income: $2,200 (2 units renting for $1,000 per month)*Pro Rated For When I Move In A Year- Cash flow: $337 per month ($2,200 - $1,862.66 = $337.34)- Down Payment: $8,095 (including closing costs and cost of inspection)- Cash on cash return: 11% ($337 x 12 = $4,048.08 Then $4,048 / $113,000 = 0.035 = 35%)