(approx 35% of yearly rev there comes from Dec, Jan, February) We would airbnb our current place in Jersey which would do relatively well during those months, but it difficult to get a pulse when the data is all over the place. 

Maybe you find family money, borrowing from bank of mom and dad, or uncles, relatives and friends and family. 

Standard homeowner's insurance typically covers personal property, liability, and the structure of your home, but it may not fully cover incidents related to tenants.

Syndications add layers of complexity (securities laws, investor relations, underwriting larger loans), which can be tougher while working full time.

Property Condition & Amenities: it’s important to, “Maintain to the Neighborhood.”Key metrics for each Property Class:Class A Properties:Tenant Pool: Majority of FICO scores 680+, no convictions/evictions in last 7 years.Tenant Default: 0-5% probability of eviction or early lease termination.Section 8: Class A rents are too high and won’t be approved.Vacancies: 5-10%, depending on market conditions.Cashflow vs Appreciation: Typically, 3-5 years for positive cashflow, but you get highest relative rent & value appreciation.Class B Properties:Tenant Pool: Majority of FICO scores 620-680, some blemishes, no convictions/evictions in last 5 years.Tenant Default: 5-10% probability of eviction or early lease termination.Vacancies: 10-15%, depending on market conditions.Cashflow vs Appreciation: Typically, 1-3 years for positive cashflow, balanced amounts of relative rent & value appreciation.Section 8: Class B rents are usually too high for the Section 8 program.Class C Properties:Tenant Pool: Majority of FICO scores 560-620, many blemishes, but should have no convictions/evictions in last 3 years.

Regardless of what you do, the important part is you always need to plan for being able to cover the cost of the interest of the money borrowed via HELOC.

And now next is health insurance.

Live in one unit, rent the others, and let your tenants cover the mortgage while you learn the business.

The dislike of FHA loans, particularly by experienced realtors who represent the seller, is twofold: FHA loan appraisals are more aggressive in the "nitpicky-ness" of relatively minor cosmetic issues, and buyers with FHA loans tend not to be as financially sound and reliable as other loan programs. 

Throw in that many first time home buyers are also the ones who could get hit the hardest with the potential increases in health insurance, rising taxes and property insurance.