Start small with strategies like house hacking, leveraging your hands-on skills for value-add properties, and building a strong team or network to reduce risks.

Many of them might be skilled folks but they are not always the best estimator and business person. 

If you are not planning to live in the property, then you are not going to qualify for an FHA loan.

Work with a qualified tax advisor on filing all of this including filing the 990T return for the IRA.

Quote from @Michael Klick: Quote from @Jonathan Greene: HELOCs are fine, but keep in mind that you really only want to use 50 percent of less (each) of your available equity just so you aren't creating a problem that you can't solve later if the value of your personal residences fluctuates.If you both have W2 jobs though, have you looked into getting qualified together and just getting a loan, 10 percent down each?

Depending upon the Lenders if you qualify, you can get up to 100% in Rehab Financing and/or up to 90% LTV on Purchase Costs.

There are several articles that do an exceptional job of explaining who, what, where, why and how tax payers qualify for the ‘STR Loophole’ listed here:The Short Term Rental Tax Loop Hole: A Game Changer for W-2 Wage EarnersThe Short Term Tax Rental Loop Hole: What Investors need to know The implications on the Oregon and California Coastal STR market is a strengthening buyer pool for luxury rentals in the $750-1.5M+ range.

Most mortgages aren't "assumable" (able to be transferred) and even if it is the new borrower would need to qualify the same as the original borrower.

Rev Proc 2008-16 does create a safe harbor for your investment intent at 2 years of investment use coupled with  some other qualifiers.  

No one is "timing" the market, they just are not qualified.