That means 8 roofs, 8 foundations, 8 interior units that need painting, 8 exteriors that need painting, 8 units that might need carpet/vinyl/tile, 8 hot water heaters or a single boiler, 8 AC or evaporative coolers (if there are coolers, have there been leaks?)

Roof 10 years old. 

While the HOA fees do diminish cash flow and can adjust year to year, it seems to me that by purchasing a condo within an existing HOA could actually save you money (no large expenses, i.e. water heater, roof, etc.)

Either your home inspector was a complete moron or your new management company is taking a slightly leaking or weak foundation wall and trying to make a major paycheck on it.  

It's a fantastic home with updated AC, furnace, water heater, roof, etc. but it's extremely dated.

.$42,000 Purchase$15,000 Closing, New Roof, Chimney, and AppliancesAfter these repairs the property would be worth $70,000 - $75,000 or could get rent for $850 /  mo.  

We've cracked down on maintenance inspections since they failed to tell us of a big leak in the roof.  

In the early phase of discussion with any new client who, say, wants a roof inspection or any other inspection likely to incur work, I tell them in clear and certain terms that I do both inspections and construction, but I will not work on any property I've inspected, or inspect any property on which we've worked.

The thing others have missed is that a motorized vehicle WILL leak some fluid at some point.

This is another place where a building inspector could help warn you about any major repairs that may be coming due in the near future (new roof, new heating/AC, etc)Property Filter strategyProperty must be in price ranges of 25000 to 675,000 with the maximum including repairs.Must be maximum 25 years oldMust NOT have nearby UN-clean properties Ex/ non maintained lawn, crumbling roof/structure, torn gates, abandoned cars and possible current crime related houses Must not have major issues or structure issues,examples include an unstable foundation, and big holes in the roof or walls.Seller must be willing to pay 50 percent closing costsMust not have taxes that go over 8250 annually Must have at least 25% in equityMust have the potential rent value of at least 500Must not have more than 2 mortgages on the propertyDocumentation to ask the seller for:Leases/rents for the past year, Tenant applications and screening procedures, tax returns for the past 2 years, also income and expenses for the past year, current rent roll (including unoccupied units, unpaid rents, and concession losses), List of improvements on property in the last 10 years.Documentation of all loans against propertyAvoid all illegal conversions or constructions.Avoid houses with no electrical wiring or AC or plumbing or if these criteria are severely damaged.Property must have cash flow of at least a total of 100 dollars.Plan for Financing At 18 years of age I will start investing in Multi homes with a loan called 203b mortgage (an FHA loan).This will allow me to only put up 3.5 % as a down payment and have a very low interest rate of around 3.5-3.9%.This loan requires me to live in the property for 1 year + though and have mortgage insurance, and so I will live in one unit while my other 1 or 2 units are rented out while I attend college.My down payment and closing costs will be from saved money from jobs in fast food and other work areas from beforehand.I will use 30 year fixed rates.Steps to take in the whole process:Have my attorney write up my contracts beforehand which include ways to exit before closing, financing terms, closing costs being 50/50 split , make sure the sellers future property info is accurate and reliable or else he is accountable and everything else he/she recommends Have my loan prequalified beforehandMake a lowball offerNegotiate until an offer is accepted or you have hit the buying price limit, or the 70% ruleOnce an offer is accepted inspect the house thoroughly by an appraiser and an inspector and take lots of pictures and videosrequest these forms:Leases/rents for the past year, Tenant applications and screening procedures, tax returns for the past 2 years, also income and expenses for the past year, current rent roll (including unoccupied units, unpaid rents, and concession losses), List of improvements on property in the last 10 years.Documentation of all loans against propertyIf the deal is still sweet, go ahead and continue with closing and finalize the deal Hire a property manager with at least 3 recommendations and question him about      these areas of work, also ask for a complete list of all past clients contact numbers.