We didn’t find a joint investment, but I found an off-market deal and invested with my dad separately.

Welcome to the real estate hive.. are you open to exploring off-market listings through your network? 

Are there any guidelines or best practices (ie: rewiring such a property would be more valuable than updating insulation).Is it something you need to ask the insurance company about to get, or is all this determined in the initial interview with the potential insurer?

Considering recent market insights, reallocating your $300K brokerage account into a multifamily property while keeping your townhouse rented could be advantageous.Warren Buffett’s Berkshire Hathaway has accumulated a record amount of cash, suggesting a cautious stance due to potential market overvaluation.

Quote from @Michael Calvey: Quote from @Sebastian Bennett: Can we re-name the reviews category: Rent to Retirement Marketing.

To determine what to offer on a rental property:Determine reasonable market rent, NOT the highest!

Have you found certain markets or zoning factors that make the process smoother?

For your seller its an effective sales price of ask - 2% using your assumed $500,000 thats $490,000, a real good offer depending on your market.  

Quote from @Robel Nessro: How is President Trump going to effect the Real Estate Industry, will it benefit the investors or impact the market and investors?  

There's no real hard and fast way or only 1 way or doing your first 2 points. your subject line suggests you're not looking to go to a large shop like a JLL or a CBRE which honestly I don't blame you those offices are usually pretty bloated.As far as monthly costs, if you are going to individually get a costar or other such license you are probably looking at $500-$1000 a month pretty easy in overhead once you have office dues, mls dues, marketing, etc.