Commercial Land Lease Opportunity - Creative Advice Needed!

[Jarred F.]

First time poster on Biggerpockets!

An 88 year old friend of mine owns 1.47 acres of very prime land located on a busy retail corner. She has owned it for 50 years. She does not want to sell it, but lease it. She would be content with $6K-7K a month for a long-term (20-99 year) land lease. She has no mortgage. Long-term land leases in my area for similar size are going for $9K-$11K a month. So I believe there is opportunity, but am trying to creatively come up with the best option.

Other factors: Included on the property is her very old house and two very old commercial buildings (3,000 sf and 1,000 sf). She would like to continue to live in the home until she passes. So this may be a few years (she is doing well). She currently operates out of the 3,000 sf selling Florida novelty items (just to stay busy) but wants to retire. The building may be rentable, but in the current condition it would only generate maybe $2K/mo. She leases the other 1,000 sf building for $1K a month.

Land leases in my area of like kind are asking $70K-$90K per acre on loopnet. So, I believe the potential for a good land lease (pharmacy, bank, etc) could be upwards of $9K-$11K per month.

My issue is that the land couldn't afford to pay the $6K-$7K a month now, but eventually I would be able to sublease for a long-term ground lease for $9K-11K month and make a good profit. With her not wanting to give up her house (until she passes) an institutional ground lease now (pharmacy, etc) would not make sense as it would cut the usable sf of the land by 25% (if the city would even allow mixed use to continue). 

I'm hoping the above is clear. If I'm missing some details, let me know. One idea is to see if the zoning is OK for a car lot and clearing all buildings, but her home. But that would probably only generate $4K/mo. I could do the same for a plant nursery. 

Or I could put her under long-term land lease where I will manage all her property for her and she would get 100% of the proceeds. Upon her death and upon us finding a suitable long-term land lease she would get $7K/mo and we would be able to sublease for $9K-$11K with planned increases and make the difference as profit. But I'm not sure this would entice her.

Another idea could be to put her under contract with a 6 month contingency and see if any larger developers would assign the deal with a fee paid to me. 

Do any of you have experience in this area? Any creative ideas? Am I missing something?  I do feel there is opportunity, but not sure how best to structure the deal. Thank you in advance!!!