Repairs made while the property is your primary residence are not deductible, but improvements can increase your cost basis, reducing future capital gains tax when you sell.

I am looking to purchase more rental properties in the near future.

I am looking for any recommendations on how to properly scale this idea over the first few years conservatively and not wanting to over use leverage and debt by starting small in duplex and being open to triple/quadplex in the future if the right opportunity presents itself.

They originally wanted 360k, but the mortgage would have the property running negative for the foreseeable future until all renovations are done, which I won't do. 

With the future being so uncertain I realized there was a need to do more than just rely on my job for financial security. 

Get an attorney and get these losers out then hire a property manager to properly vet any future tenants! 

Over the years every single time I went over his house to hang out we would talk about money, investing and the future we were building.

If millenial homeowners can't even change their home's air filters, or snake a toilet, or change the oil in their car, that's guaranteed future business for HVAC companies, plumbers, mechanics, and those places all need a place to conduct business in.The commercial mortgage pricing software I use has somewhere around 50 different asset classes in it.

But also with low debt or free and clear property that they can easily access any time in the future with a cash out refinance.

A goal gives you direction, purpose, and excitement for the future.