I would suggest taking the route of option 2 or 3, so not only are you saving over 10k in rent per year but the residents help in paying down the debt.

Any repair issues the new acquisition has you will feel to much greater magnitude due to the property carrying a lot of debt.

Using a 1031 to upgrade to a two-family could help you reduce or eliminate the $1,000 out-of-pocket expense you’re paying now.Also, condos often come with HOA fees that limit cash flow, so be mindful of their impact.

I have 880 credit score, decent savings, and no other debt except for 300K mortgage on my primary residence (worth $1.5 million).

Hey , yea thinking more on this, having other positions would be a tough sell.My strategy for substitution of collateral is to get better debt terms on an investment I want to buy.Ex.

I am looking for any recommendations on how to properly scale this idea over the first few years conservatively and not wanting to over use leverage and debt by starting small in duplex and being open to triple/quadplex in the future if the right opportunity presents itself.

They have made major sacrifices and in most instances they have sunk fortunes into their portfolio to pay down the debt. 

However, deeds in lieu of foreclosure can be subject to judicial attack by their grantors and their grantors' creditors.Grounds for attacks on deeds in lieu of foreclosure include the following:• That the deed was an equitable mortgage - that the parties intended the deed to be given as security for a debt and that the deed was not an absolute conveyance.• That the deed is either a preferential or fraudulent transaction within the purview of the provisions of the federal Bankruptcy Act or any other related state law.• That the deed is a device to clog a mortgagor's right of redemption.• Unfairness of the consideration.• Coercion, fraud, oppression, duress, and undue influence.• That the deed is not subsequent to the execution of the mortgage but contemporaneous with it.• That the grantor/mortgagor was insolvent at the time of the execution of the deed.An estoppel affidavit (executed and acknowledged by the grantor/mortgagor, attesting to the fairness of the transaction, the consideration exchanged, the value of the property, and other factors showing an intention to make a genuine transfer) or a recital (inserted directly in the deed) are supporting documents used to forestall challenges to these transactions.State law and local title standards must be consulted in regard to the consideration and treatment of deeds in lieu of foreclosure.What a GREAT post!   

any lender wants to know how you plan to service the debt.

An update one year later after this post, I now have:- Got my property and casualty license and wrote 370+ policies in a year- Saved up a few more thousand dollars in investable cash, paid off $20K in debt and raised my credit score by 100 points- Launched a direct to seller cold email marketing campaign and generated leads for cheap- Got connected with a few real estate investing communities like Subtle Asian Real Estate and Pace Morby's SubTo- Aggressively read and studied as much as I can get my hands onThat being said, I decided to run a marketing campaign to generate distressed seller leads in Phoenix, Arizona, mostly because:1.