With the lease option, I worry that while I'm happy with the price today, I could see a drop in value of the property over the next couple years and have trouble obtaining a conventional loan without injecting more capital into the property.All thoughts or opinions are greatly appreciated.Edit to add:My question is geared toward loans that are obtainable by people with 700+ credit scores and strong income in relation to outgoing 

If I were the old landlord, I would allow my outgoing tenant to pay me, in advance for the 2 days (or even a week) so he could stay there until your place was vacant.You could also just be up front and tell the new tenant, "the old tenant has not moved out yet.

The tenant was very cordial and outgoing.

As per your inputs you have outgo of $1021 per month for 12 months.

Just check the unit specs for the delta between incoming vs outgoing temps. 199k BTU's are not equal.

I am not always the most out-going so sometimes getting a total stranger (like a listing agent) on the phone can be difficult or “scary” for me.

However, if you feel like that's the only way you can do it and you have a solid plan b for if you hate it or it doesnt work out--go for it!!!!

I spoke to outgoing tenants respectfully, even when they were mad at me.

Last year I was in your shoes, listening to podcast after podcast, reading books, devouring articles, how-to's, and talking to realtors.The story going around in my head was--is this industry, career, and life just for the ultra-outgoing, super-confident movers and shakers?

I would concur with him, find something that you can add value to, but isn't a full gut rehab, especially on your first deal.You can do exactly what he suggests, take advantage of the low down payment on an owner occupied purchase, add some value, rent it out, go buy another one, and repeat.