So weighing the tax breaks of longer holds against the risks and opportunity costs, I believe Bruce's strategy makes less sense for me personally in my situation and my market, but works very well for him.This is what I love about RE, it is so nuanced and location specific that a guy like Bruce can do it 1 way, and be completely right for his situation and market, and another guy like me can do the opposite and also be right (I believe) for my situation and market ... different markets, different conditions, different strategies ... this may be confusing to newbies, but I think the value for others is not in the strategy to copy, but in understanding the thought process and rationale behind it ... then they can apply a similar thought process to their market and situation to custom fit a strategy for themselves.

I have a natural draw towards the "flipping" sector, as my background tends to lead me in that direction, but at this point only consider this as a secondary form of investment, wanting to invest the majority of my time and money into buy and hold properties.My short-term goal would be to flip a few homes to help develop substantial capital to purchase my first multifamily property (triplex/quadplex), in which I would like to live/rent/self manage.

(I.E. squatters, fires, and the demo costs if the city when the city requires you to remove it after say year 15 due to its dilapidated condition.)

Cap rates and property condition is a good place to start as well as the rent roll. 

Depending on the size of your units, have you looked into ductless air conditioning?

I know several wholesalers who do this.If you are buying at an auction or county sherif sale- you can buy with your own cash and resell to anyone you want in whatever condition you want.

It turns out, the house is in one of the best locations in town and is in incredible condition (has never been rented to a person outside of his family). 

But the value really depends on the condition and location of the complex. 

After 12 months, your property should be in good condition to be able to pass a bank inspection, and the appraisers will be able to use sales comps for similar small houses (even if there is no any 1 bedroom sales) and adjust accordingly.  

Good Morning,I was looking through a few HUD listed properties last night that are for sell in my area , and I was reading through the Property condition report/summary documents , and am a bit confused by what they mean.For instance:The Property Condition Report shows that there is NOT a Dishwasher present , as well as stains in the Bath Tub that can NOT be removed The Property Condition Summary shows ( via Escrow description ), that there is some needed Plumbing to be done ( $300 ).