We just can't make up our minds.....?

Option A: Keep the $450k (investment) and $650k (future home) houses we own and do nothing
Option B: Keep the 2 houses and buy a $150k pure investment
Option C: Sell the $450k and buy a $350k investment
Option D: Sell the $450k and buy a $450k investment/possible future home in different state
Option E: Sell the $450k and buy a $650k future home in different state

I guess there are some variables I have not factored in here but this is what it boils down to. What would you do and why?

There are too many unknown variables to make an informed and helpful answer. Are the houses mortgaged? if so what is rate, equity of each, and current income from them if any. You need to look at the housing market and the effect it will have on your homes. ( is the area around them being rezoned dense housing) as to moving to another state, 650K in one state may buy you a luxury mansion, while in another a simple 3 bedroom rancher. Go to your bank and ask to speak with one of their investment councillors. Usually a free service, they can help you decide on your long term goals, the best way to reach them . Based on what you have provided as information and not knowing your financial status, (will you need money for living expenses? or is that already covered, or are you needing to use the funds you are investing now. I would decide where I wanted to retire too. What Type of home I would be happy with, and what I would need to live comfortably. Then I would consult a specialist as to the safest, and most profitable way to do it.
Keep in mind the older a home gets the more it costs for upkeep. A home that is making you money now may start to cost you money, time, and headaches later on

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