When either of these properties goes on the market after our market in Denver has normalized the new owners will probably see a net loss on the property.

Just food for thought.

The smaller, portfolio lenders are more concerned with their total loan loss and less concerned with ongoing holding cost loss. 

Obviously, I am operating at a loss but I am wondering how I could structure a deal to change this.

This has my insurance in the cost as well.Obviously, I am operating at a loss but I am wondering how I could structure a deal to change this.

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.

However, after 2 job losses between 2009 and 2011, our savings are gone and we are starting over financially.

Rent loss? 

I did have one tax ramification that caught me off guard when I got married two years ago: before I got married, my income was such that I got to deduct 100% of my real estate losses (depreciation, etc.) because my AGI only included my income alone.  

Its still losing significant money in terms of cash flow which is typically an absolute no-no.But given you're in california and given your other properties are covering the losses, I don't think this is crazy thinking.