In my experience, the farther in advance I tell my tenants the better they react.I've heard some landlords say that they raise the rent when their costs go up (such as property taxes) to cover the increase, but that makes no sense. 

I'm finding the hard part is more finding properties that are in a good location and also don't have restrictions on short term renters (either hoa or local regulations).I've reached out to owners with the same basic offer (increase rent, cover repairs up to a certain amount) and most people are hesitant to even discuss it, so i think it's a sheer numbers game and being ready to buy a property when one shows up that matches my criteria

And if there's a cap-ex hiccup that comes along there's no equity for the <insert form of debt here> to cover that.  

I'd be able to cover the loan payment based on what I'm typically offered for a housing allowance.

Any thoughts on how to creatively cover the down payment and rehab costs for a second property given the above scenario?

You and your family would basically be covered for life.

You can search by keyword, such as real estate, and zip codeDo not assume that any particular group covers the area around their meeting location. 

That should cover all of your bases.Don't focus on or worry about the tenant evictions situation.  

So it's 500 bucks up front for new people (unless referred to me by one of my regular investors) and that covers me physically going to 10 houses.

The next option I thought of was buying a rental property with money I have saved up, renting that property and using its cash flow to cover the rest of my dads mortgage.