I am a rookie RE investor.

-Question: What are some smart financing options to still fix the leak knowing that I’ll probably sell in the near future?

Every job your tenants have today will disappear in the foreseeable future.

Sellers Info-Main interest: minimizing capital gains/taxes, preserving estate for his kids-SFH free and clear, no mortgage, purchased 30 years ago for ~$150k-Currently acting as landlord, very likely doesn’t want to continue in this capacity My info:-I want to cash flow the property now -I want to purchase the home now or in the future Property info-No tenant, rent comps $2600-2800-Current comps of $290k-320kI don’t know the sellers full financial picture.

Once you have an idea of the cash flow in the future state you can then spend most of your time determining the funding for renovations to get the property to that point.

Yes you will find an agent that will continue to write contracts for you, but you have to ask yourself and you really getting great service?  

Maybe I'll branch out in the future, but not sure yet.Slow flipping or house hacking would be great, but I have a 4 month old and we love our house, so that's off the table.I guess I'm looking at ways to minimize risk when starting out.

@Joseph Chiofalo is a good local lending resource and dually licensed RE broker, good for some high level market insight.

An updated roof mitigates potential water damage in the future.

That is a huge win and your future self is thanking you already.