You should continue to invest in your retirement funds especially if you are getting an employer match.I think locking in a low rate on a 30 year mortgage today would be a good idea for your rental property but only if you have the resolve to use the 'extra' cash flow you will receive from a lower payment to aggressively attack your other debt.

Some income may not qualify, seasonal jobs that are not regularly performed, part time jobs that are not performed on a regular basis, employment income received from a job or line of work less than two years, child support payments that are not paid through any court system with a history of on time payments.I would insist on saying that "Compensating factors effecting credit, income, employment and criminal histories will be considered to the benefit of the applicant".

There are some techniques to convert your rental income into W-2 income, but bear in mind that you are taking income that is not taxed for self employment taxes and making it taxable. 

Negotiating Short Sales you have some control as too the timing of closing the deal as they are many stalling tactics you can employ. 

Like any other 1099 contractor like an agent or mortgage broker, it's considered self-employment and we all need at least 2 years of tax returns to get traditional financing again.

I’m 27 working a W2 job, but looking to be self employed within 2-3 years.

As you start building your investment portfolio, there's a few things I'd keep in mind: Income: For conventional loans, it is important to have stable salaried employment and to avoid employment gaps.

In this case I would only be borrowing 40% of value of the property because the rest would be funded by the seller.I do also have 35K in a rolled over IRA account from a previous employer. 

I am a self employed contractor (sole proprietor).

@Roy Oliphant I will be interested in counties with the right investment dynamics of population, employment and growth prospects.