We own a 7 unit apartment building at the beach and would like to replace our present bank loan with private funding of some type.  The banks in USVI are VERY risk adverse resulting in major processing costs and restr...

Better for resale and if one bathroom has issues that need to be resolved, your tenants can use the other one while it is getting fixed.

We have worked with probably a dozen different contractors/roofers to resolve exterior water penetration issues and they have all been hit or miss.

While my tenants have been great, dealing with all the issues and repairs that have come up have been a real headache.

Title issues, seller issues, non-refundable deposits, no inspection period, lending issues, appraisal issues, liens, IRS liens, city liens, no wills, unpaid back taxes, solar liens, and all kinds of other crazy stuff.   

If you do a  search of this forum you will find that financing properties in CR is an issue, though the nature there and lifestyle is very attractive

I've started my own journey about a year ago in wholesaling and I'm working towards the ultimate goal of multi-family and commercial investing.

https://www.biggerpockets.com/forums/51-tax-legal-issues-con...

5.How do you handle maintenance issues and respond to emergencies in your homes? 

I am not sure how you are intending to manage, but beware the local labor pool is not the greatest and I think you may have some issues finding either decent management or finding decent workers if you intend to self manage.