Other than it being a additional cost to do business and financing being more difficult under a LLC as long as you have adequate insurance coverage there is little other difference. 

Just make sure you have enough liability coverage ($1M if possible) to cover any sort of potential issues. 

I aim to redirect my career (no more travel) and supplement my work with investing.

Could we use outside income to supplement the S Corp?

If you venture into the area, I'd be sure to get appropriate insurance coverage (i.e. wind, flood, etc.) just in case it happens again! 

Any advice on coverage costs/options?

I recently had a challenge securing affordable insurance with good coverage.

In my experience, if the pool has no slide or board, and has a gate around it, good insurance with a high liability coverage isn't much more than a house without a pool. 

If you put stock in CAP rates (I don't) you are looking at below 5%.Additionally, you would require a larger downpayment to bring your Break-Even-Ratio (BER) below 85% and your debt coverage ratio (DCR) over 1.25 (in my experience, commercial lenders like to see 1.4 or better).While market rent may be greater, remember you are paying for the current performance of the business, not it's potential -  which will require further work and capital from you to achieve.  

They jack up other fees And they routinely skip checking for “unrecorded liens” such as code violations, utilities, etc and Rxclude them from coverage in the B Rxvludions.