Owner of a Mortgage Company and new IG pool owner here. On the topic of getting rid of PMI you must have a 24 month history of PMI with your current mortgage company to request dropping PMI, otherwise you will need to refinance if you what out of PMI with < 24 months history. Best thing to do is to contact your current mortgage company and ask them their requirements to eliminate PMI.
Financing a pool. I typically take my clients to banks that have what's called a second mortgage pool loan. They take the improved value with the pool and loan off this, this would be a good option for folks with little value into their home. Check with your local credit unions or banks to see if they have this option.
Hope this helps.

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