@Hannah Noble You need to be very careful and do deep due diligence on a leasehold condo deal subject to a ground lease. Don't be afraid of the deal, just do your due diligence. Here are the headline red flags to look out for:
1 - Leasehold Interest. When you purchase the condo you will own the improvements (the condo) but you will not own the land beneath the condo. That's not unusual (a condo association or HOA would normally own the land anyway). The unusual part in a leasehold condo is that an investor owns the land and will charge you ground rent. So red flag one is determine the ground rent and pay attention to ground rent escalation clauses. The ground rent could be very high (20K plus a year and rising) plus leasehold owners often try to sell just before a rent escalation period.
2 - Ground Lease. The ground rent, rent escalation and length of the ground lease are the critical parts of this deal. At the end of the ground lease ownership of the improvements usually return to the ground owner. You need to check if you can automatically renew the lease. If you can not renew the ground lease, or you can't renew it at a reasonable rate, the value of the condo will significantly decrease, down to zero , as the ground lease nears its end of term. In short, your condo will decrease in value each year. Red flag 2 is check the right of lease renewal and red flag 3 is pay careful attention to rent escalation.
3 - Financing a Leasehold Condo. Fannie Mae underwrites leasehold mortgages so getting competitive finance isn't difficult but does require a mortgage broker who understands the product. The red flags are that lenders may not offer leasehold mortgages in your area, lenders require the ground lease to run at least 5 years past the mortgage term (you have 37 years left .. that's getting tight) and the condo dev still needs to be warrantable. Most older leasehold condo developments are no longer warrantable. If not warrantable you will not get a loan. Even if you have the cash to buy, it will be difficult to resell.
Some ideas - value the condo based on the comparable cost of renting the same unit. If the numbers pencil then think of it as a nice rental for you personally in a great area (few minutes from the beach). It could also be a really nice short term rental as you can buy for far less than a comparable fee simple condo and the cash flow could be excellent. Just accept that you need to make enough money now to walk away from your purchase price later.
The biggest idea - figure out how you can be the land owner in one of your future deals.