I currently have a homeowners plan with Allstate and plan on asking them if they have something like a short term rental rider plan that I can add in addition to my current plan.

Quote from @John Paul Palace: Our plan was to invest locally, however our market here is tough.

I recently had a client purchase a duplex in Forest Park here in the western suburbs with this exact plan in mind.

Ultimately, I plan on investing myself either going the house hacking route or doing a flip. 

(b) Is it okay to talk to multiple realtors at the same time (I'm thinking it would be better to have a separate realtor with lots of market knowledge and experience in each of the mentioned locations) or should I only plan to use one?

When we moved, we turned it into a rental, hoping this would be the start of our real estate journey—something we’d like to continue once my husband retires.Some key details:My husband is active duty and will retire in 3 years.We have one final move coming up this summer to Raleigh, NC.Our current debts are crippling us—the high interest makes it tough to stay afloat every month.The plan me and my husband are thinking bout:Sell the rental property.Use the proceeds to pay off all our debts, set aside emergency funds and a down payment for our next home.Free up $1,500/month from debt payments, and that also can stash in a high-yield savings account.Regain full VA loan entitlement, allowing us to purchase a multifamily home and use the house hacking strategy for up coming move.Avoid capital gains tax, since April marks five years of ownership, and the tenant’s lease ends in May.This wasn’t our original plan, and we hate the idea of using our equity to pay off debt.

If you plan on staying 10 years and can handle the initial negative cash flow, you likely will do great (prop 13 helps).

It's worth about $350,000 and no liens.I was thinking about making it a midterm rental or a short-term rental but it would require quite a bit of work and would require getting a home equity loan.Also considering selling and buying a turnkey str.I do plan on leaving the country and I'm not sure where I'll end up.Would love to hear the pros and cons from all you professionals.

Real Estate investing has changed my life and I plan to help others do the same.

With your background, I have no doubt you're starting on the right foot.How many properties are you planning to start with?