A second mortgage or HELOC might allow you to unlock some funds without losing the 3.25% rate.- I recommend avoiding condos. 

So either you pay for the repair out of the idle cash in your account, file an insurance claim and use those funds, or rollover/transfer funds from another retirement account to cover the cost. 

May be you meant that the IRA has deferred-tax funds and not Roth?

3) Your $250k with 30% down => about $750k (you also need funds for closing costs, taxes, etc.)

I’m currently working towards another rental property (duplex or larger) but I know I still need funds.

I have not done it personally but have some insight, maybe my reply may boost your post to someone with more experience in it. 

Shadow/mentor a person doing it.

A landlord policy can be a commercial policy or a personal lines policy.It's the same as asking if you should buy a single family rental or a 1 unit building.Focus on the coverages and disregard the name of the policy.

I also have a personal relationship with my contractor so got a massive price break. 

It is also worth noting that property management is often closer to 30% of gross rent for a short-term rental due to the much more intensive hands-on management compared to a typical 10% for long-term and as such, I agree with recommendations above that medium term rentals may provide the best of both worlds if you are able to tailor proximity to a local need, e.g. hospitals and travel nurses.Again, happy to relay my personal experiences in the area if you're interested.Best of luck,Patrick