However, our tenants plan to vacate this March and have expressed interest in purchasing the home.I'm contemplating whether it's more advantageous to sell or retain this asset.

It's at the point where I'm contemplating selling the property as is and moving on.

Your contemplation of the cash-buy strategy in the current real estate market is indeed a prudent one, given the rising interest rates and the challenge of finding cash-flowing properties.

Shoot, they might have been contemplating getting new furniture for a while and willing to sell you the old stuff in their house for cheap! 

I'm contemplating if that would be worth it for getting the advice/expertise they have. 

@Dorothy Butala @Patrick Philip   Hello Patrick - Get your track shoes on because the advice Dorothy is offering is going to cause you to  run away from every management company in the nation that could even contemplate handling your homes. 

In light of this, it is prudent to contemplate the rationale behind the decisions of seasoned investors within the locality who chose to forgo this opportunity.

I am trying to find investment opportunities out of state, so I was contemplating building a house down there as a rental and see if it would be cost effective vs buying and renovating, or even just buying a turn key home. 

Never had the need before: this is the first time I've contemplated buying a fixer-upper (all my others were purchased move-in ready).My team is currently composed of those roles you'd expect of a buy and hold investor (RE agent, property manager, repairman, insurance & mortgage brokers, attorney, bookkeeper & CPA, etc.); I've assembled this team over the last 4 years of investing in the town (including several trips there to meet them, and buy property, in person).Put another way: I'm *way* more confident buying in this town halfway around the globe than I am buying in the city I live in.  

No one can tell me if “another market” is justified by another 65 mile difference or whether up to lender to decide I’m contemplating moving title into LLC anyway and taking my chances on asking for forgiveness or selling if doe on transfer happens.